By Erwin Szeto | Co-Founder, iWIN Wealth Planning 

Recorded: June 2026 

Host: Erwin Szeto, The Truth About Financial Independence for Canadians 

Guest: Byron Darlison, Founder Rise Vision, Certified Metronomics Coach, Accelerator Coach EO Toronto

He Worked 60 Hours a Week for 25 Years. Then He Installed a System and Sold for an 8-Figure Exit.

Byron Darlison on Business Operating Systems, the Great Wealth Transfer, and What Financial Independence Actually Looks Like.

Byron Darlison started Rise Vision in Toronto in 1992. He ran it for 30 years without raising a dollar of outside equity. For 25 of those years, he worked 60-plus-hour weeks, watched the business oscillate between good years and terrible years, and never fully understood what was making it unpredictable. 

In year 25, he hired a business coach and installed Metronomics as his operating system. In the 5 years that followed, profits went from break-even to 20% sustained net margins. Revenue growth went from low single digits to 15 to 20% per year. His personal work week dropped from 60-plus hours to under 10. He promoted his COO to run the company and stepped back to chairperson. In year 30, he sold Rise Vision to AUO Display Plus for an 8-figure exit, with no earn-out and no employment clause. His team still runs and grows the business today. 

He now coaches a small number of founders privately using Metronomics and serves as Mentorship Chair and Accelerator Coach at Entrepreneurs’ Organization Toronto. He publishes free frameworks, AI prompts, and tools at darlison.com. 

This is a conversation about what it actually takes to build a business that works without you, why most founders never get there, and why the next decade may be the best buying opportunity for small businesses in Canadian history. 

25 Years of Hard Work, Inconsistent Results 

Rise Vision did not start as a digital signage company. Byron spent years building software for Reuters to power LED screens on trading floors, then moved into banks, retail, and gradually what the industry started calling digital signage. For most of those years, the company was spread across 117 different industries. It had good years and bad years. The team was talented and deeply loyal, with some people staying more than 20 years. But consistency was elusive. 

Byron describes the dynamic bluntly: the team was exceptional at fighting fires. Nobody was in charge of fire prevention. There was no clear accountability structure, no defined priorities, and no rhythm that held the business to a standard quarter over quarter. 

He tried to fix it himself. He worked through Scaling Up, the Great Game of Business, Scrum, Basecamp, and lean startup principles. He spent a year attempting to self-implement a business operating system and made limited progress. Looking back, he identifies 4 reasons why it did not work. He was simultaneously the person building the accountability system and the person the system was supposed to hold accountable. When you are a player on the field, you cannot see the whole field. The team had watched him launch initiatives before and learned to wait them out. And without someone who had visibly done it before, there was nothing to counter the quiet skepticism that this time would be any different. 

What a Business Operating System Actually Is 

Byron defines a business operating system simply: a set of rituals at a specific cadence, captured in artifacts, that becomes religion. 

Not a framework you run for a quarter and then move on from. A rhythm that becomes so embedded that breaking it is unthinkable. Meetings that happen at the same time every week. Scorecards that are updated and reviewed in every session. Accountability structures where every person knows their domain, their critical number, and exactly what a good day looks like for them. 

The key insight he shares: the founder has to be the first to demonstrate the discipline. If the founder shows up late, everyone shows up late. If the founder skips meetings, everyone skips meetings. The system only works if the leader makes it non-negotiable for themselves first. 

For a company with a long history of operating in a loose way, he warns it takes about a year before the system starts to stick. The tell is when team members start self-correcting each other, saying we do not do it like that, we do it like this, before the founder has to say it. At that point, the organization has internalized the rhythm and it starts to compound. 

5 Years That Changed Everything 

The results Byron describes after installing Metronomics are specific and verifiable: 20% sustained net margins for 5 consecutive years, revenue growth of 15 to 20% per year, and a work week that dropped from 60-plus hours to under 10. Cash reserves built to many multiples of annual operating spend. 

At some point during this period, Byron realized something that very few founders are willing to admit: he was no longer the right person to be running the business day to day. His COO was. He promoted his COO to head of company, stepped back to coach the executive team, and found that running the business in under 10 hours a week, he was actually running it better than he ever had at 60. 

The return on the coaching investment, calculated conservatively over 5 years, was approximately 270 times its cost. 

How He Sold With No Earn-Out and No Employment Clause 

When Byron went to sell Rise Vision, the business was already operating without him in any active role. He was chairperson in name. The company had a proven operating system, predictable recurring revenue, a leadership team that ran and grew the business independently, and cash reserves exceeding a year of operating costs. 

That combination made the negotiating position straightforward. The company did not need to drop in revenue during a drawn-out acquisition process because Byron had no active role to distract from operations. He could devote full time to the negotiations without the business suffering. By the time the deal closed, revenue had grown by approximately 20% from where negotiations started. 

His advice for founders approaching an exit: the business needs to look like a machine to any acquirer. Predictable, self-running, not dependent on the founder. If it does, you can set your terms. If it does not, you are selling a job, and the buyer will price it accordingly. 

The Owner’s Outcome Framework 

One of the most practically useful frameworks Byron shares is what he calls the owner’s outcome: the exercise of getting precise about what you actually built the business to give you, before you make any strategic decision. 

He observes that most founders have a vague idea of freedom when they start, but never translate that into specific terms. How many hours do you want to work? What income do you need? What is your risk tolerance? What does your life look like at the 3-year mark if the business is working? 

Without that clarity, the business wanders. Every shiny object looks like an opportunity. Every crisis demands a response. There is no benchmark to measure whether the company is actually serving the founder’s goals or drifting away from them. 

This framework resonates particularly strongly in real estate. Erwin makes the connection in the conversation: he has coached real estate investors since 2010 and regularly encounters people whose stated why is more time with family, but who have bought a small business, in the form of a rental property, an hour from home, with a customer, the tenant, who has more rights than most business clients. The two do not reconcile. Byron’s response: they haven’t done the homework. 

The Definition of Strategy Is the Word No 

Byron’s framing of strategy is one of the cleanest distillations of the concept: if you know exactly what you want, 90% of what you see is noise by definition. Strategy is the discipline to say no to that noise, over and over, until what you are building becomes so specific and so well-understood that you win your market almost by default. 

Rise Vision’s pivot to K-12 digital signage in North America came from data, not instinct. After years of serving 117 different industries, the team looked at where the growth was consistent, where they won competitive deals, and where customers stayed forever. Education kept coming up. It was not glamorous. The procurement process was slow. The revenue per customer was not large. But the fit was undeniable. 

Focusing on that single market, with a single core customer, is what allowed the business to stop being spread across everything and start building genuine expertise. Once the product was built for one specific buyer, the sales and marketing costs dropped, the product team had clarity, and the competitive moat deepened every year. 

The Founder’s Dilemma 

Byron names the thing that kills most founder-led businesses before they ever reach an exit: the founder who is the hero. The one who jumps into every problem, gives the answer, and then wonders why the team never develops the capacity to solve problems without them. 

His reframe is simple and memorable. Instead of solving problems, ask: what do you recommend? Instead of giving the answer, ask by what date and how will you know it’s working? The goal is to make the person who owns the problem also own the solution, the measurement, and the learning. The founder becomes an editor and a mentor, not a firefighter. 

For anyone buying a business from a retiring founder, this is a critical due diligence signal. If the current owner is involved in everything, is the hero of every story, and cannot name a single decision the team makes without them, the buyer is not acquiring a business. They are acquiring a job. Byron puts the implication plainly: the team will not be able to independently execute once that founder exits. 

The Great Wealth Transfer and Why Boomer Businesses Are the Buying Opportunity 

Byron spent a day with Keith Cunningham, author of The Road Less Stupid, in Austin, and came away with a view he shares directly: there has never been an opportunity like this in our history. More businesses are coming up for sale right now than has ever happened before. Supply is high. Qualified buyers are scarce. Valuations reflect that. 

His sharper point is this: many of these businesses are badly run. Not terminal, not broken, but operating well below their potential because the founder never installed accountability, never defined a core customer, never built a system. That means the stated EBITDA is artificially low, the multiple is priced off that artificially low number, and a competent buyer who can install the missing infrastructure can earn back the purchase price in a fraction of the typical cycle. 

Cherry’s acquisition of a second accounting practice from 2 retiring owners in 2024 is a version of exactly this. The practice was well-established, the clients were loyal, and the owners were ready to exit. The opportunity came not despite the transition, but because of it. 

AI Running a 14-Agent Software Pipeline While Byron Sleeps 

Byron’s current project is a software development operation running entirely on AI agents. 14 agents, an orchestrator that manages the work queue, and a process where Byron tells the system what is in the backlog before he goes to bed and reviews the completed work at 6 a.m. The cost in human terms: approximately $300,000 a month in traditional development resources. His actual cost: a fraction of that. 

His advice for founders exploring AI: the one-off experiments are easy. Creating something reliable, scalable, and secure is not. The hard work is thinking through the architecture, defining the roles each agent plays, and building the methodology that makes the whole system trustworthy before you depend on it. 

He has published AI prompts on darlison.com that compress the time required to work through his core frameworks, including owner’s outcome, core customer analysis, and company values discovery, from days of consulting time to under an hour of structured AI-guided work. 

FAQ 

What is Rise Vision? 

Rise Vision is a cloud-based digital signage software company founded in Toronto in 1992 by Byron Darlison. It grew to serve organizations in over 100 countries, including schools, hotels, and universities. In 2022, it was acquired by AUO Display Plus, a Taiwanese industrial display manufacturer. 

What is Metronomics? 

Metronomics is a business operating system developed by Shannon Susko. It combines strategy, execution, and team alignment into a quarterly rhythm of meeting cadences, scorecards, and accountability structures. Byron Darlison used it to transform Rise Vision from a break-even company into a profitable, self-running business before selling. 

What is the owner’s outcome framework? 

The owner’s outcome is a framework Byron uses with every founder he coaches. It asks the founder to define precisely what they want their business to give them, in terms of income, hours, risk tolerance, and life design, before making any strategic decision. Without this clarity, businesses tend to drift toward whatever is urgent rather than whatever is important. 

What is the great wealth transfer and why does it matter for Canadian investors? 

Baby boomers own a massive number of privately held businesses in Canada. As they retire, those businesses need buyers. Because many of these businesses are poorly systemized and priced off artificially low earnings, buyers who can identify and fix the operational shortcomings can acquire businesses at significant discounts to their real earning potential. 

How is Byron using AI in his business? 

Byron is running a 14-agent AI software development pipeline from his home. He briefs the orchestrator each evening on the work backlog, the agents process tasks overnight, and he reviews output in the morning. He estimates the traditional human cost of equivalent output at approximately $300,000 per month. He has also published free AI-guided prompts at darlison.com for working through business frameworks. 

Join Me Live: Free Training on the $100,000 Investment Loan Strategy

I’m hosting a free training on the strategy that produced the returns I mentioned above. It’s hybrid: in-person at the iWIN office in Oakville, or join on Zoom from anywhere.

Here is exactly what I will walk through in 90 minutes:

1. The complete $100,000 investment loan structure
2. The math — what $433 a month actually buys you over 5 and 10 years
3. Every loss scenario — what happens when the market drops 20%, 30%, 40%
4. How this fits alongside, not replacing, a real estate portfolio
5. Live Q&A — bring your questions, bring your skepticism

Two dates to choose from. Both cover the same content — pick whichever fits your schedule.

Saturday June 27, Hybrid (Oakville + Zoom) — 9:00am ET, hard stop 10:30am. In-person seats are capped at 40 and they always go. If you want to be in the room, register today.

Tuesday July 7, Zoom only — 8:00pm ET

The Bottom Line 

Byron Darlison spent 25 years running his company the hard way. Not because he was not smart, not because the team was not talented, but because he never installed the structure that would have let the business work without him carrying it. Once he did, everything changed: the margins, the growth rate, the work week, and ultimately the exit. 

The lesson is not specific to SaaS companies or digital signage or Toronto tech founders. It applies to any business, including real estate portfolios that have turned into jobs, rental operations that never scaled, and accounting practices changing hands in Ottawa. The question underneath all of it is Byron’s question: what did you build this for, and is it delivering that? 

If the answer is no, the system is the fix. And the system is learnable. 

To Listen

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/60-Hour-Weeks-for-25-Years–Then-10-Hours-a-Week–Then-an-8-Figure-Exit–Byron-Darlison-e3l82cf 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/37865c02-70d7-42ff-a027-d45158fff0c8/the-truth-about-financial-independence-for-canadians-60-hour-weeks-for-25-years-then-10-hours-a-week-then-an-8-figure-exit-byron-darlison

Apple: https://podcasts.apple.com/ca/podcast/60-hour-weeks-for-25-years-then-10-hours-a-week/id1100488294?i=1000774184213

Audible: https://www.audible.ca/podcast/60-Hour-Weeks-for-25-Years-Then-10-Hours-a-Week-Then-an-8-Figure-Exit-Byron-Darlison/B0H6MTFLX3?source_code=ASSGB149080119000H&share_location=pdp

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts 

Every guest on TAFI is here because they have done something worth studying. Milena Simsic did it faster, younger, and with less of a head start than most. Pay attention to the pattern, not just the result.

Disclaimer: 

As a committed advocate for transparent and responsible investing, I disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer. I am also a licensed insurance agent with Open Concept Financial Group. The investment loan strategies discussed are for educational purposes only and are not a guarantee of approval or performance. Past performance is not indicative of future results. Every investor should do their own due diligence. 

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Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

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Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

By Erwin Szeto | Co-Founder, iWIN Wealth Planning 

Recorded: June 2026 

Host: Erwin Szeto, The Truth About Financial Independence for Canadians 

Guest: Milena Simsic, Founder, WindSocial Realty; Publisher, Windsor Real Estate Insider; Host, Windsor REI Social 

Milena Simsic made $300,000 in commissions in her first year as a realtor. She had no prior real estate connections, no social media following, and no marketing budget. What she had was a willingness to show up on TikTok and Instagram before anyone else in her market was doing it, and a formula she figured out in public. 

Three and a half years later, she runs Windsor’s most recognized investor-focused real estate team, publishes a newsletter with over 9,000 subscribers, and hosts a real estate investor community of 3,000 members that fills rooms with 100 to 200 people twice a year. She has also replaced her virtual assistant with Claude AI, built her CRM systems in an afternoon, and is now teaching other realtors how to do the same. 

This is an episode about what financial independence actually looks like when you build it from scratch, in a mid-sized Canadian city, with no inherited advantages. It is also, quietly, one of the clearest illustrations of why TAFI rebranded: the path out of the rat race does not always run through a rental property. 

The Windsor Market Right Now: What Is Holding and What Is Not 

Windsor has always been the most affordable large city in Ontario, and that affordability has acted as a cushion during the broader Canadian real estate correction. According to Milena, single-family homes in Windsor have held relatively steady because demand for primary residences has not collapsed the way it has in markets dependent on investors or short-term renters. 

The segments that have softened are student rentals and multi-unit investment properties. The immigration policy shifts of 2024 and 2025 hit student rental demand directly, and investment properties have followed. But for anyone buying a single-family home in Windsor, the fundamentals remain intact: low vacancy rates, a growing population, and a cost base that cannot be matched anywhere else in Ontario at the same level of amenity. 

Milena made the comparison plainly: for an investor deciding between a Toronto condo and a Windsor house right now, she said the Toronto condo has really tanked. The Windsor house, by contrast, still has a tenant market and a price point that works. 

🎙️ Listen to the podcast 

The Growth Drivers: EV Plant, Gordy Howe Bridge, and a Billion-Dollar Downtown 

Windsor’s economic story in 2026 is being written by 3 major developments. The EV battery plant is now operational and has brought thousands of jobs and thousands of new residents into the city. Traffic, which was always a non-issue in Windsor, has become a mild inconvenience, which Milena describes as a good problem to have. 

The Gordy Howe International Bridge, which was expected to open in March 2026, has been delayed by political interference from the U.S. side. The delay has created uncertainty, but the bridge remains a long-term economic catalyst for cross-border movement and commerce. 

The third driver is a billion-dollar downtown redevelopment announced by Farhee Development, with a major build expected to break ground in 2026. For a city the size of Windsor, a billion-dollar downtown investment is transformative. Milena notes that the timeline depends on when the developer wants to start, but the project is committed. 

$300K in Year One: How She Did It With No Connections and No Prior Social Media 

When Milena entered real estate, she made a decision that most new agents do not make: she treated the business like a marketing operation from day one. She had never used social media personally before getting her license, had no following, no network in real estate, and no referral base. 

She went on TikTok and started posting Windsor real estate content before anyone else in her market was doing it consistently. By the end of her first year, she had made $300,000 in commissions, entirely from TikTok and Instagram leads. More than half her clientele came from the Greater Toronto Area, drawn to Windsor by the price differential and guided to her by the content she was publishing. 

She attributes the result to spotting where the highest-leverage play was and going all in before the market caught up. The same logic has since driven her into AI. When she saw what AI could do for her business, she moved before most of her peers understood what they were looking at. 

Windsor Real Estate Insider: From a Client Resource to 9,000 Subscribers 

The Windsor Real Estate Insider started as a private resource for Milena’s clients, a document she called the Windsor Price Guide that helped investors understand the local market. The response from clients was strong enough that she decided to turn it into a proper publication. 

Since launching the magazine last year, it has grown to over 9,000 subscribers, all organic, with no paid acquisition. When you search Windsor real estate on Instagram or TikTok, Milena is the first result. The newsletter feeds from that visibility, and the visibility feeds from the newsletter. The two surfaces compound each other. 

Windsor REI Social, her investor community, operates on a similar logic. It began as monthly meetups that were drawing 30 to 70 people. She eventually moved to a biannual format and the events now draw 100 to 200 attendees, with guests traveling from outside Windsor including Toronto. 

Replacing a Virtual Assistant With Claude AI: What She Built and How Long It Took 

Milena’s AI implementation story is one of the most concrete in the episode. She was on the verge of hiring a second virtual assistant to handle CRM management, client responses, and backend administrative tasks. Instead, she set up Claude AI using the Cowork desktop tool and replicated the systems her VA had been running. 

The result was faster turnaround, higher accuracy, and a significantly lower cost than any human hire she could have made. She notes that she did not need any coding experience to build the systems. She wrote out the processes the way she would have written them for a human assistant, step by step, and Claude ran them. 

Her assessment of the competitive implications is direct: the top agents that implement AI are going to absorb all the business because no unassisted agent can compete with the response time and output volume that AI enables. She is now building a community for realtors who want to learn how to do what she did. 

EXP to Real: Why She Switched and What It Means for Realtors Choosing a Brokerage 

Milena announced on the show that she is leaving EXP for Real, an online brokerage that she describes as more focused on agent quality and community than on recruitment volume. Her critique of EXP is specific: many of the top earners in the EXP structure have never completed a real estate transaction. They joined to recruit, not to sell. 

Real, she says, actively discourages the pyramid recruitment dynamic and instead focuses on building a quality agent community. For Milena, the brokerage is primarily a platform to operate her own brand underneath. She does not believe the brokerage matters much to an agent’s success in terms of leads or training, but she values the culture and cost structure at Real over what she had at EXP. 

The Health Crisis That Doubled Her Business 

Two years ago, Milena developed thyroid issues she attributes in part to the stress of her first years in real estate, which coincided with a market peak and then a correction, all while she was working 40 to 60 hour weeks. She describes reaching a point where her health was failing and she recognized she was the bottleneck in her own business. 

The pivot started with salsa dancing, which she took up to feel better in her body after the autoimmune diagnosis. It cascaded from there into improved diet, therapy, changes in her sleep and work structure, and a recognition that working smarter and being present was more productive than grinding more hours. Since making those changes, her business has more than doubled. 

She entered the Windsor pageant a second time in 2026, roughly 3 years after her first attempt in which she did not place. This time she placed first runner up. She frames the second attempt as a personal milestone to close the chapter from 3 years ago and measure how far she had come. 

Advice for Young Canadians: Build Your Skill Set, Buy a Business, Stop Making Excuses 

In the closing exchange, Milena’s advice for young Canadians under economic pressure is blunt and specific. Build your skill set. Learn continuously. If you can, find a way to acquire or start a business, because employment is becoming less reliable as AI and economic shifts reduce traditional job availability. 

She notes the irony that while the economic environment is genuinely harder for young people, it has also never been cheaper or easier to acquire skills, start a business, or find a mentor. AI gives anyone access to expertise that previously required expensive professional services. The resources exist. The excuses are running out. 

On the business acquisition side, she endorses the vendor take-back financing model, noting that a significant proportion of businesses listed for sale are prepared to offer seller financing, making zero-down acquisition genuinely possible for a prepared buyer. 

Quick Answers 

What market does Milena Simsic specialize in? 

Windsor, Ontario. She focuses primarily on investor clients, more than half of whom come from the Greater Toronto Area. 

How did Milena make $300K in her first year as a realtor? 

Entirely through TikTok and Instagram content. She started posting Windsor real estate market content before any other agent in her market was doing it consistently, and built her lead pipeline from those platforms with no prior social media experience. 

Is Windsor real estate a good investment in 2026? 

Milena’s view is that single-family homes in Windsor have held up well. She says the Toronto condo has been harder hit than the Windsor house. Windsor has low vacancy rates, a growing population, and major economic development underway including an operational EV plant and a billion-dollar downtown redevelopment. 

What is Windsor REI Social? 

A real estate investor community of 3,000 members that Milena runs in Windsor. It hosts biannual events drawing 100 to 200 attendees, with speakers and networking focused on Windsor and southern Ontario real estate investing. 

How is Milena using AI in her real estate business? 

She replaced her virtual assistant with Claude AI using the Cowork desktop tool, which now handles CRM tasks, client responses, and backend administration. She built the systems herself in an afternoon with no coding experience. 

Why is Milena switching from EXP to Real? 

She says EXP’s culture prioritizes recruitment over agent quality, with many top earners having never completed a real estate transaction. Real actively discourages that dynamic and focuses on community and agent development instead. 

Join Me Live: Free Training on the $100,000 Investment Loan Strategy

I’m hosting a free training on the strategy that produced the returns I mentioned above. It’s hybrid: in-person at the iWIN office in Oakville, or join on Zoom from anywhere.

Here is exactly what I will walk through in 90 minutes:

1. The complete $100,000 investment loan structure
2. The math — what $433 a month actually buys you over 5 and 10 years
3. Every loss scenario — what happens when the market drops 20%, 30%, 40%
4. How this fits alongside, not replacing, a real estate portfolio
5. Live Q&A — bring your questions, bring your skepticism

Two dates to choose from. Both cover the same content — pick whichever fits your schedule.

Saturday June 27, Hybrid (Oakville + Zoom) — 9:00am ET, hard stop 10:30am. In-person seats are capped at 40 and they always go. If you want to be in the room, register today.

Tuesday July 7, Zoom only — 8:00pm ET

The Bottom Line 

Milena Simsic did not start with a network, a marketing budget, or a family in real estate. She started with a willingness to show up consistently in public before anyone else in her market understood why that mattered. That instinct, which she applied first to TikTok and then to AI, is what separates her story from a hundred other first-year realtor stories. 

What makes this episode particularly relevant for the TAFI audience is the portability of the model. Milena is not a real estate investor in the traditional sense. She is a business builder who happened to start in real estate. The leverage she used was not bank financing on a rental property. It was audience leverage, technology leverage, and the compounding effect of publishing consistently over time. Those tools are available to anyone. 

For investors who are tired of the LTB, tired of rent control, and tired of carrying properties that no longer cash flow, Milena’s arc is a useful reminder that the rat race has more than one exit. 

On Spotify: creators.spotify.com/pod/profile/erwinszeto/episodes/From-Factory-Worker-to-300K-Realtor–Milena-Si… 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/897f73b2-6d14-46d0-ab11-1ba2ab39a0f3/the-truth-about-financial-independence-for-canadians-from-factory-worker-to-300k-realtor-milena-simsic

Apple: https://podcasts.apple.com/ca/podcast/from-factory-worker-to-%24300k-realtor-milena-simsic/id1100488294?i=1000772208538

Audible: https://www.audible.ca/pd/B0H4VX8QJV?source_code=ASSGB149080119000H&share_location=pdp

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts 

Every guest on TAFI is here because they have done something worth studying. Milena Simsic did it faster, younger, and with less of a head start than most. Pay attention to the pattern, not just the result.

Disclaimer: 

As a committed advocate for transparent and responsible investing, I disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer. I am also a licensed insurance agent with Open Concept Financial Group. The investment loan strategies discussed are for educational purposes only and are not a guarantee of approval or performance. Past performance is not indicative of future results. Every investor should do their own due diligence. 

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Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

By Erwin Szeto | Co-Founder, iWIN Wealth Planning 

Recorded: May 2026

Host: Erwin Szeto, Truth About Financial Independence for Canadians

Guest: Carlos Rodriguez

Quick story before we get into this week’s guest. 

Back at our September 2025 iWIN Wealth Summit, I walked through what I’ve been calling the 4-to-1 strategy. The idea is straightforward: $100,000 of investor capital combined with a $300,000 investment loan from the bank for a total of $400,000 deployed into professionally managed and index stock funds, including S&P 500 exposure. 

Since that September presentation, the market has appreciated more than 13%. After management fees and borrowing costs at 5.2%, that translates into an estimated 40.6% return on the investor’s original $100,000. Leverage cuts both ways, of course, and suitability matters tremendously. But if you’re a real estate investor or someone pursuing FIRE, you already understand this principle intuitively. We’ve all used prudent leverage in real estate for decades. 

Speaking of how leverage cuts both ways, Canadian real estate is in decline. Hamilton in particular is down 9% year-over-year, leading the entire country, as reported in the Globe and Mail. I’m glad I sold some Hamilton properties when I did. I wish I’d sold more. 

Especially our Hamilton duplex. The tenant stopped paying rent. The LTB hearing got postponed, then postponed again. Seven months in, I’m $12,000 deep in lost rent, a couple thousand more in paralegal bills, and still waiting. Even with all the best screening practices, I couldn’t have foreseen the tenant’s health failing and his white-collar tech job laying him off in the same year. I’m holding the bag as a private social safety net at my own expense. 

This is the world I’m operating in. And it’s the context that makes today’s guest worth your time. 

Meet Carlos Rodrigues 

Carlos Rodrigues spent 20 years in Canadian financial services. He holds licenses in mutual funds, life insurance both levels, and was a full mortgage broker, not just an agent, running four to five agents under him. He even started building out his own investment fund before the Canadian compliance costs shut that plan down. 

So when somebody with that résumé tells me the math in Ontario doesn’t work anymore, I pay attention. 

Today, Carlos is an active real estate investor focused on Cleveland, Ohio. He’s on the tools, on site, and driving four and a half hours each way from Hamilton to do it. He runs BRRRRs, joint ventures, and Section 8 rentals. He’s bought houses for as little as $70,000 that now appraise for over $170,000. 

This isn’t a fantasy pitch. Carlos is honest about what active cross-border investing actually looks like. 

The $70,000 Duplex Near the Cleveland Clinic 

The headline deal in this episode is a 3,000-square-foot duplex Carlos bought for roughly $70,000, including a $24,000 wholesale fee. The property sits within a two-minute drive of the Cleveland Clinic, one of the largest hospitals in the United States, in a zip code that’s actively gentrifying. 

The condition was rough. The main-floor toilet was on a diagonal and falling through the floor. But the bones were there. After renovations, the duplex appraised at $170,000. 

This is the kind of math that doesn’t exist in the Golden Horseshoe anymore. 

Section 8 Economics That Don’t Exist in Canada 

One of the most eye-opening parts of the conversation was Carlos’s breakdown of how Section 8 (US government rental assistance) works for landlords. 

He’s getting 20 to 30 percent above market rent through the program. He shared one tenant in the Coventry area, a retired nurse, who rents from him for around $1,400 per month. Of that, she pays $14. The federal voucher covers the rest. 

“We’re considered the socialist country,” I said to him at one point, “but we don’t have anything like this in Canada.” 

His strategy intentionally targets Section 8 because it builds a strong rent base. If the broader economy turns down and tenants in other rental classes start losing jobs, his voucher-backed rent keeps flowing. 

There’s risk on this side too. Federal funding can change. But compared to my Hamilton duplex, where a job loss meant seven months of zero income and a paralegal bill, the contrast is hard to ignore. 

What the US Lending Market Is Doing Right Now 

Carlos shared an email he just received from a US broker offering 100% loan-to-cost financing. That’s 100% of the purchase price plus the full renovation budget, lent against the after-repair value. 

This is the kind of headline that triggers 2008 comparisons. Both of us went out of our way to address that. As Carlos put it, in 2008 lenders were putting a mirror in front of borrowers’ faces and lending if it fogged. That isn’t what’s happening now. These loans go through proper appraisals, lead-safe certifications, rental licensing inspections, and the rest of the US regulatory apparatus. But the credit is loose, and that’s worth knowing. 

For context, just a few weeks before that email, brokers were quoting Carlos 90% loan-to-cost. The market is moving. 

The Joint Venture Partner Who Panicked 

Carlos didn’t sugar-coat the operator headaches. His most painful recent story involved a joint venture partner who, between Carlos leaving the site for a Home Depot run and returning, expanded the renovation scope from $65,000 to over $100,000. 

“The unfortunate thing with joint venture partners,” Carlos said, “is when people start to get uncomfortable, they start trying to shift to alleviate that pain. And sometimes they do things that, well, over-renovate.” 

It’s a useful warning for anyone considering JV deals across a border, especially when one partner has Ontario-market mental models and the other partner is dealing with Cleveland-market realities. The numbers in Cleveland support a different finish level, different price points, and different exit timelines. Mismatched expectations cost real money. 

The Contractor Problem 

Cleveland is busy. Contractors are scarce. Carlos’s contractor ghosted him a week before closing on his current project. 

He also raised a less-discussed reality: the immigration crackdown in the US is hitting the construction labor pool. Many of the most reliable workers in his market are of South American descent, and ICE enforcement has made them cautious about advertising their services publicly. Phone numbers are gone. Contractors now communicate through Instagram DMs and voice-over-IP. Even legal workers are wary. 

That tightens the supply of skilled trades. If you’re going into Cleveland for active renovation work, this is a real cost you need to budget around. 

Cleveland Appreciation: Real Numbers 

Carlos was disciplined about underwriting. His own deals assume 1.5 to 2 percent annual appreciation. He expects 2 to 4 percent over the next five years. 

Recent actual appreciation in Cleveland: 7 percent year over year. 

The gap between what he underwrites and what he’s actually getting is what builds margin of safety into his deals. This is the same lesson Sarah Coupland made last week, working backward from conservative resale values rather than chasing the optimistic case. 

The Side Yard Program 

One small detail that stuck with me: Cleveland has a side yard program where if your principal residence sits next to a vacant lot owned by the land bank, you can buy that lot for $100. If your investment property sits next to it, you can buy the lot for $500. 

Compare that to the Golden Horseshoe, where lots run hundreds of thousands of dollars. These are different markets with different math. The strategy you use in one doesn’t transfer to the other. 

The Bottom Line 

Canadian real estate isn’t dead. But the conditions that made it a passive vehicle for the average investor aren’t like they used to be. If you want to be an active operator, treat real estate as a business, and drive four and a half hours each way to do it, the Carlos Rodrigues path is open to you. 

If you want passive, you need to look elsewhere. Landlord-friendly US markets through the right partners. Leveraged stock-market positions through investment loans. Small-business acquisition. These are the paths the show will keep covering. 

Diversify. Pacify. Get your time and your peace of mind back. 

That’s the next chapter.

Want the Whole Investment Loan Strategy Walked Through Live? 

This Saturday, May 30, 2026, I’m hosting a free training on the strategy that produced the 40.6% return I mentioned at the top of this post. It’s hybrid: in-person at the iWIN office in Oakville, or join on Zoom from anywhere. Hard start at 9:00am Eastern, hard stop at 10:30am. 

In those 90 minutes, I’m walking through: 

1. The complete $100,000 investment loan structure 

2. The math, what $433 a month actually buys you over 5 and 10 years 

3. Every loss scenario, what happens when the market drops 20%, 30%, 40% 

4. How this fits alongside, not replacing, a real estate portfolio 

5. Live Q&A, bring questions, bring skepticism 

In-person seats are capped at 40 and they always go. If you want to be in the room, register today. 

Saturday May 30, Hybrid (Oakville + Zoom): infinitywealth.ca/20260530 

Tuesday June 2, Zoom only at 8pm Eastern: infinitywealth.ca/20260602 

Both events cover the same content. Pick whichever fits your schedule. 

To Listen:

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/20-Years-in-Canadian-Finance–Now-He-Only-Buys-70K-Cleveland-Duplexes–Carlos-Rodrigues-e3k0v4j

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/d6ad4f99-c233-4397-884a-d8d94e54b29f/the-truth-about-financial-independence-for-canadians-20-years-in-canadian-finance-now-he-only-buys-70k-cleveland-duplexes-carlos-rodrigues

Apple: https://podcasts.apple.com/ca/podcast/20-years-in-canadian-finance-now-he-only-buys-%2470k/id1100488294?i=1000770024019

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Disclaimer: 

As a committed advocate for transparent and responsible investing, I disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer. I am also a licensed insurance agent with Open Concept Financial Group. The investment loan strategies discussed are for educational purposes only and are not a guarantee of approval or performance. Past performance is not indicative of future results. Every investor should do their own due diligence. 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

By Erwin Szeto | Co-Founder, iWIN Wealth Planning 

Recorded: May 2026

Host: Erwin Szeto, Truth About Financial Independence for Canadians

Guest: Sara Coupland, Real Estate Investor

Real estate investing is easy to talk about when markets are rising, financing is available, and the portfolio is growing. It gets much harder when life changes, assets must be sold, and the market no longer supports yesterday’s valuations. 

In this episode, Erwin sits down with Sarah Coupland, a long-time Ontario real estate investor, coach, construction operator, and owner of TAG Property Management. Sarah has been investing since 2007, built a personal portfolio of more than 60 doors, and manages about 300 units for herself and other investors. 

She also specializes in the kinds of properties most investors avoid: distressed multifamily buildings, mixed-use assets, older properties, and renovation-heavy projects that banks often will not finance. Now, as she works through the sale of her portfolio during divorce, she is also rebuilding from the other side using joint ventures, private money, and a more intentional strategy. 

Selling a Portfolio in a Difficult Ontario Market 

Sarah’s portfolio once included more than 60 doors. Today, because of her divorce, she is liquidating assets she had expected to keep long term. That process has forced her to reassess market values, buyer psychology, and the emotional side of letting go. 

One of her biggest lessons is corporate structure. Most of her properties were owned in corporations where she and her spouse were 50/50 shareholders, but Sarah held the controlling shares. That made the disposition process smoother because she could deal with lawyers, realtors, and purchasers without every decision becoming a back-and-forth negotiation. 

For investors building portfolios with spouses, partners, or joint venture investors, this is a major lesson: ownership and control are not always the same thing. The structure you set up when times are good can determine how manageable things become when life changes. 

Distressed Multifamily Is Not for Beginners 

Sarah specializes in highly distressed properties. One featured example is her 12-unit mixed-use building at 144 King Street West in Cobourg. The property had major deferred maintenance, a fire order against the third floor, wildlife inside the building, and units that were not suitable for habitation. 

The project was massive. Sarah purchased the building for approximately $700,000, structured an 80% to 85% vendor take-back mortgage, capitalized the interest into the purchase price, used private money and deferred payments, and ultimately ended up with about $1.7 million invested after a renovation budget of roughly $1 million. 

The property is now listed around $2.6 million, with roughly $21,000 per month in rent and a cap rate around seven, according to Sarah’s estimate during the conversation. Tenants pay utilities, the building has been extensively renovated, and much of the heavy lifting has already been done. 

The story is a strong example of forced appreciation, but it also highlights why these deals are not simple. Heritage requirements delayed the project by roughly six months over window requirements. An engineering miscalculation created an additional $80,000 electrical issue. The renovation took about two and a half years instead of the expected year and a half. 

That is the reality of distressed real estate investing: the upside can be significant, but the execution risk is real. 

Why Old Buildings and Mixed-Use Properties Can Work 

Many investors avoid old buildings, heritage districts, commercial units, and tertiary markets. Sarah often leans into them because lower competition can create better pricing. 

Her strategy is not to buy anything old blindly. It is to understand what can be fixed, what needs to be budgeted, what the market will support, and whether the numbers still work after realistic contingencies. She has also found that commercial tenants can add stability, and that commercial landlord-tenant issues are often simpler than residential issues under Ontario’s Landlord and Tenant Board system. 

That said, financing can be difficult. Mixed-use properties often do not fit neatly into standard CMHC or bank financing boxes. Sarah has used private lenders, vendor take-backs, seconds, and non-bank financing to make projects work when traditional lenders would not. 

Investor Appetite Is Returning, but Discipline Still Matters 

One of the most interesting parts of the conversation was Sarah’s take on today’s Ontario real estate market. On the sales side, she is seeing buyers still searching for discounts and often not believing the market has bottomed. On the acquisition side, however, she is also seeing aggressive activity. 

One off-market property she analyzed received 11 offers in three days and sold about $60,000 over asking. Another rough Peterborough triplex from a wholesaler sold over asking despite needing extensive work. 

Sarah’s conclusion is balanced: investors are starting to come back, but she refuses to chase deals. She works backward from conservative resale values, renovation budgets, investor return requirements, and contingency buffers. If the numbers do not work, she lets the deal go. 

That discipline matters in a market where comparable values can move quickly. Sarah shared a recent flip where expected resale values dropped from about $550,000 to $530,000 during the renovation period, and the property ultimately sold for $505,000. The deal still made money, but only because the numbers had enough room. 

LTB Challenges, Renovictions, and the Reality of Bad Buildings 

Sarah also spoke directly about Ontario’s landlord environment, including renovation-related bylaws and the pressure placed on private landlords to carry low-rent or non-performing assets. 

Her view is pragmatic. She respects housing needs, but believes governments should not expect private landlords to subsidize low-income housing indefinitely, especially when mortgage costs, repairs, insurance, and taxes continue rising. 

In distressed projects, Sarah says she often approaches tenants honestly. If the building is unsafe, she explains the work required, offers compensation, helps with moving, and documents the process properly. She is not evicting for sport; she is trying to fix buildings that may have water pouring down walls, electrical problems, structural issues, or unsafe conditions. 

For Landlord and Tenant Board matters, her advice is simple: communicate clearly, document everything, be honest, and bring evidence. If you made a mistake, admit it and move on. If you are at the board, make sure you are there for a valid reason and can support your position. 

Becoming a Full-Time Investor Is Not Retirement 

Sarah offered one of the most honest answers in the episode about becoming a full-time real estate investor. Too many people market it as “retire today” or “quit your job and become financially free.” Sarah’s reality was different. 

She worked as a financial advisor at CIBC, renovated after work, ate on the go, and spent evenings and weekends doing the hard labour. When she eventually left her job, she did not simply jump into the unknown. She created supplemental income through property management, bought a fourplex, and worked with joint venture partners and private money. 

Her warning is important: becoming a full-time investor is not retirement. Often, it is trading one job for another. The key is to build systems, income streams, a team, and a business that can eventually give you time back. 

Sarah’s personal goal was to be off when her daughter was off during the summer. With coaching and intentional planning, she eventually built rules around her acquisitions. If she did not have an offer accepted by the end of March, she stopped buying until after summer. That discipline helped her protect the life she was investing for in the first place. 

Education, Action, and Coaching 

Sarah credits much of her growth to education and community. She mentioned Durham REI and Quinton de Souza as important influences, especially in learning about RRSP mortgages, joint ventures, flips, BRRRRs, and vendor take-back mortgages. 

Her final advice for investors is straightforward: get educated, build your network, take action, and consider coaching when you are ready to move beyond basic investing. Her coaching is not aimed at complete beginners. It is better suited for investors who already own properties and want to move into multifamily, renovations, portfolio strategy, and more intentional investing. 

Sarah’s story is a reminder that financial freedom is not always a straight line. Sometimes the portfolio changes. Sometimes the market changes. Sometimes life changes. But with the right structure, conservative numbers, strong relationships, and the willingness to rebuild, real estate can still be a powerful path to wealth for Canadian investors. 

How to Connect with Sarah Coupland 

Sarah can be reached through her website at SarahCoupland.ca or by email at Sarah@TAGProperties.ca. Investors interested in her listed properties can also connect with Anita Bongers-Lewis and Chris Lewis at Doors to Wealth Real Estate. 

Quick Answers 

• How many units does Sarah Coupland manage? 
  Sarah Coupland manages about 300 units through TAG Property Management, including properties for other real estate investors. 
• How many doors did Sarah Coupland own? 
  Sarah’s personal real estate portfolio was over 60 doors before she began liquidating assets during her divorce. 
• What type of real estate does Sarah Coupland specialize in? 
  She specializes in distressed multifamily, mixed-use, and older Ontario rental properties where value can be created through renovations and better management. 
• Why does Sarah Coupland use private money and joint ventures? 
  She uses private money and joint ventures because many distressed or mixed-use properties do not fit traditional bank financing, especially during construction or major renovations. 
• What is Sarah Coupland’s opinion on the Ontario real estate market? 
  Sarah believes Ontario still has real estate investing opportunities, especially in small multifamily properties, but investors must be conservative with numbers and contingencies. 
• What advice does Sarah give about becoming a full-time real estate investor? 
  She says becoming a full-time investor is not retirement; it is often trading one job for another unless you build income, systems, and a team. 

Want the Whole $100,000 Strategy Walked Through Live? 

This Saturday — May 30, 2026 — I’m hosting a free training called the Zero-Down Wealth Strategy. It’s hybrid: in-person at the iWIN office in Oakville, or join on Zoom from anywhere. Hard start at 9:00am Eastern, hard stop at 10:30am. 

In those 90 minutes, I’m walking through: 

1. The complete $100,000 investment loan structure 

2. The math — what $433/month actually buys you over 5 and 10 years 

3. Every loss scenario — what happens when the market drops 20%, 30%, 40% 

4. How this fits alongside (not replacing) a real estate portfolio 

5. Live Q&A — bring questions, bring skepticism 

In-person seats are capped at 40 people and they always go. If you want to be in the room, register today. 

Saturday May 30 — Hybrid (Oakville + Zoom): infinitywealth.ca/20260530 

Tuesday June 2 — Zoom only at 8pm Eastern: infinitywealth.ca/2026060

Both events cover the same content. Pick whichever fits your schedule. 

The Bottom Line 

Canadian real estate isn’t dead. But the conditions that made it a passive vehicle for the average investor are gone. If you want to be an active operator and treat real estate as a business, more power to you. If you want passive, you have to look elsewhere — landlord-friendly U.S. markets, leveraged stock-market positions, small-business acquisition, and a few other paths the show will keep covering. 

Diversify. Pacify. Get your time and your peace of mind back. 

That’s the next chapter.

To Listen:

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/Rebuilding-Wealth-After-Divorce-Sarah-Coupland-on-Ontario-Multifamily–Distressed-Properties–and-Creative-Financing-e3je3l3 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/44dcec71-076a-479c-99c2-720b8f10a5aa/the-truth-about-real-estate-investing-for-canadians-rebuilding-wealth-after-divorce-sarah-coupland-on-ontario-multifamily-distressed-properties-and-creative-financing

Audible: https://www.audible.ca/podcast/ITEM-NAME/B0H1V3FMG2?source_code=ASSGB149080119000H&share_location=pdp

Apple: https://podcasts.apple.com/ca/podcast/rebuilding-wealth-after-divorce-sarah-coupland-on-ontario/id1100488294?i=1000768392581

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Why Smart Canadians Are Getting Positioned Now 

By Erwin Szeto | Host of The Truth About Real Estate Investing for Canadians 

Recorded: April 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

I’ve been doing this podcast since 2016. Almost 10 years, approaching 500 episodes. And in all that time, I’ve rarely recorded a solo episode — because this strategy is so important, and so few people are talking about it, that I needed to speak directly to you, my precious 17 listeners. 

I call it the Zero-Down Wealth Strategy. And if you’re a Canadian real estate investor who’s tired of tenant headaches, over-concentrated in local real estate, and wondering what comes next — this might be the most important thing you read this year. 

The $433 Question 

Let me ask you something. 

Would you rather invest $100,000 — or $433 a month? 

Most people hear $100,000 and immediately think: I don’t have that sitting around. But $433 a month? That’s a car payment. Most of us spend or invest that without blinking. 

Here’s the thing — they’re the same investment. 

$433 is the monthly interest cost of a $100,000 investment loan (from an institutional lender — none of that private lending crap) at today’s rate of 5.2%. One credit check. One self-reported loan application. Zero of your own capital required. No property or property appraisal. No lender fees, mortgage broker and full underwriting. 

That’s it. 

Why Canadian Real Estate Investors Are Stuck 

Before I explain the strategy, I want to acknowledge something most of us feel but rarely say out loud. 

We’re stuck. 

Inflation is real. In March 2026, Canada’s inflation rate hit 3.3% — well above the Bank of Canada’s 2% target. Just look at what it cost to build the Eglinton LRT if you want a concrete example. Money sitting idle loses real purchasing power every single month. 

We’re over-concentrated. Almost every real estate investor I meet with to discuss their investments has 80 to 90% of their wealth tied up in local Canadian real estate — all in Canadian currency. That’s not diversification. That’s concentration risk. 

Demand is weakening. Immigration restrictions, rising unemployment, softening rental demand — the outlook for Canadian investment property has changed materially. This is not 2015. 

The landlord nightmare is real. I say this as someone who’s lived it. I had a tenant deliberately flood my basement causing $10,000 worth of damage. The police couldn’t do anything. I’m currently nine months into a Landlord Tenant Board hearing just for non-payment of rent. Non-payment. Vandalism. LTB backlogs. Ontario is one of the most difficult places in the world to be a landlord right now. 

So why are we still playing the same game? 

2026: A Critical Window 

Here’s what makes this moment particularly important. 

2026 is a US midterm election year — and history has a very clear pattern: 

• 4.7% — Average S&P 500 return in midterm election years (vs. 9.5% in all other years) 

• 18% — Average intra-year market drawdown before the November election 

• 15.4% — Average S&P 500 return in the year after a midterm election 

Quarterly average S&P 500 price returns by presidential cycle (1961-2024) 

Source: Strategas Research  

We are in Q2 of Year 2 RIGHT NOW and this year should be especially volatile with this November’s midterm election deciding if Trump controls Congress or not. 

The market already dropped 9% earlier this year and bounced back 12% — exactly the kind of volatility midterm years are known for. 

The dip before November isn’t the danger. It’s the setup. 

The question isn’t whether a correction is coming. The question is whether you’ll be positioned to benefit from the rebound when it does. 

You Already Believe in Leverage 

If you’re a real estate investor, you already understand this concept — you’ve just been applying it to the wrong vehicle. 

Nobody buys investment property with cash. We put 20 to 25% down and borrow the rest. We call that smart investing. 

Around 2010 — right after the financial crisis — zero down and 5% down mortgages were everywhere in the investor community. Nobody called that reckless. We called it getting ahead. And everyone I know who took advantage of that leverage in 2010 did extremely well. 

This is the same principle. Just applied to a better vehicle — one with no landlord headaches, no appraisals, no LTB hearings, and no midnight calls. 

Two Yale Professors Proved It 

In 2010 — right after one of the worst decades in stock market history — two Yale professors published a book called: 

Lifecycle Investing: A New, Safe, and Audacious Way to Improve the Performance of Your Retirement Portfolio

— Barry Nalebuff & Ian Ayres, Yale University 

Their conclusion, backed by rigorous mathematical proof: leveraged investing, done correctly, outperforms conventional portfolios over a lifetime. 

They weren’t writing from the comfort of a bull market. They ran the math through the pain — through the dot-com crash, through 2008 — and the conclusion was the same every time. 

We real estate investors already know this intuitively. We leveraged into real estate and built wealth over the long term. This is no different in principle. It’s just a different asset class. 

The Stress Test Results 

I ran my own stress test — comparing a leveraged non-registered investment against three alternatives most Canadians swear by: 

Strategy	Result
RRSP — pre-tax dollars, tax-deferred growth	✗ Underperforms
TFSA — after-tax dollars, tax-free growth	✗ Underperforms
Non-registered, unleveraged	✗ Underperforms
Non-registered, leveraged	✅ Wins

Yes — including the TFSA. The leveraged non-registered strategy beats them all. 

I know that’s counterintuitive. We’ve been conditioned to think TFSAs and RRSPs are the gold standard. And for most people, they are excellent choices. But real estate investors aren’t most people. We walk to a different drummer. We’re looking for outsized returns — and the math confirms this strategy delivers them. 

You can verify this yourself — run the numbers in ChatGPT or Claude and it will confirm: a non-registered leveraged investment outperforms registered fund vehicles over the long term. 

How It Actually Works 

Here’s the practical breakdown: 

Step 1 — Qualify  One credit check. One self-reported loan application. No property, appraisal, mortgage broker and no full underwriting involved.

Step 2 — Borrow $100,000  100% loan to value. Zero of your own capital required. Your only cost is $433/month in interest at 5.2%. If structured correctly, that interest is tax-deductible — speak to your accountant. 

Step 3 — Invest  The $100,000 goes into a segregated fund account — think of it as a mutual fund from the insurance industry.  

Step 4 — Principal protection  This is the key difference from simply putting borrowed money into the stock market. Segregated funds come with built-in principal protection. The downside is covered. The upside belongs to you. That’s why institutional lenders are willing to lend against this — the risk is contained. 

The accounts belong to you. You sign off on everything. We coordinate the paperwork and movement of funds at iWIN Wealth Planning — but it’s your money, your account, your decision. 

Is This Right for You? 

Leveraged investing isn’t for everyone. Before you consider this strategy, ask yourself these questions — and discuss them honestly with your advisor. 

Do you have a specific financial goal in mind? 

This strategy works best when you know what you’re building toward. Retirement income? Diversification away from Canadian real estate? Getting off the landlord treadmill? Get clear on your goal before you start. 

How long are you planning to invest? 

Leveraged investing is typically more suitable for a long-term investment horizon of 10 years or more. Just like real estate — the longer you hold, the more you de-risk. This is not a short-term play. 

How much other debt are you carrying? 

Keep your debt manageable. Make sure your current debt load is under control before adding an investment loan. A good rule of thumb: your total monthly borrowing costs — including the $433/month investment loan interest — should not exceed 36% of your before-tax income. 

How stable is your income? 

A steady income helps you make the required interest payments every month without stress. If your income is unpredictable, this may not be the right time. 

What is your tolerance for risk? 

Are you comfortable with potential fluctuations in your investment value? And with the possibility that in some scenarios, leveraged investing may not outperform traditional investing? If market volatility keeps you up at night, this is not the right vehicle for you. 

Let’s talk if you answered these questions honestly and still feel confident

If I Could Do It All Again 

I want to be honest with you. 

I made the decision in 2005 — 11 years before this podcast started — to go all-in on real estate investing instead of the stock market. And I’ve built a great business from it. Nearly $500 million in investment property transactions. Four-time Realtor of the Year to investors in Ontario. 

But if I could do it all again? I would have deployed leverage earlier — into vehicles without the landlord baggage. 

Less grey hair. More money. No tenant nightmares. More time with our families. 

I think about my clients too. The ones I’ve worked with for years. We would have all made more money. We would have all been happier. That’s not a small thing. 

These are the same strategies I’m now teaching my own kids — and recommending to every client I meet. Because I don’t want non-payment of rent or tenant vandalism stealing anyone’s time away from what actually matters. My future grandchildren deserve parents who aren’t fighting about money because they have to feed the real estate’s bank account — because a tenant stopped paying or a basement flooded, which is happening ever more frequently with climate change. 

The Midterms Are November. You Have 6 Months. 

The US midterm elections are November 2026. History says markets dip before then — and then deliver some of the strongest returns of the four-year presidential cycle in the year that follows. 

You have roughly six months to get positioned. 

I’m doing a free live training where I walk through the full strategy, show you the stress test results side by side, and answer your questions directly. 

Two ways to join: 

📍  Saturday May 30, 2026 — Hybrid (In-Person + Zoom)  Doors open 8:30am · Hard start 9:00am · Hard stop 10:30am · iWIN Office, Oakville · Limited to 40 in-person 

[Register here → Wealth Planning for Canadians] 

💻  Tuesday June 2, 2026 — Webinar Only  8:00pm Eastern · Zoom · 90 minutes 

Same content both sessions. Pick what works for you. 

[Register here → Wealth Planning for Canadians] 

In-person spots fill fast. Don’t wait.

To Listen:

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/The-Zero-Down-Wealth-Strategy-How-Canadians-Use-Leverage-to-Beat-Inflation-e3il08o

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/ac823c8a-fca9-4be5-aebe-e266c178f86a/the-truth-about-real-estate-investing-for-canadians-the-zero-down-wealth-strategy-how-canadians-use-leverage-to-beat-inflation

Audible: https://www.audible.ca/pd/B0GYYHMYXG?source_code=ASSGB149080119000H&share_location=pdp

Apple Music: https://podcasts.apple.com/ca/podcast/the-zero-down-wealth-strategy-how-canadians-use/id1100488294?i=1000764468055

YouTube: https://youtu.be/ibBWxozAre8

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

SingleKey’s Mackenzie Wilson breaks down what every Canadian landlord needs to know right now — and shares product features that haven’t even launched yet.

Recorded: April 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Mackenzie Wilson

Before we get into this week’s episode, I want to share something that stuck with me.

My family attended a talk last week by Shannon Lee Simmons — CFP, bestselling author of Making Bank, and founder of the New School of Finance. The talk was put on by EO Toronto and I brought my kids. Shannon shared that many of the teenagers she works with have already given up on their financial futures. Housing feels unaffordable. Jobs are hard to find. The confidence just isn’t there.

That hit hard. But Cherry and I aren’t waiting for anyone to fix this for our kids. Our son is already working at our events earning a real wage. Our daughter starts bookkeeping for us this summer. They’re learning money, learning job skills — and yes, Dad gets a tax deduction. The point is: you fight financial despair with action, not sympathy.

Shannon also noted that because the future feels bleak, young people aren’t investing — they’re speculating. Sports betting, high-risk crypto, gambling. The casino didn’t get big by making people wealthy. The answer hasn’t changed: repeatable, boring, proven investing. That’s why this podcast exists.

Which brings me to this week’s guest.

Who is Mackenzie Wilson?

Mackenzie Wilson is Head of Business Development at SingleKey — Canada’s leading tenant screening and landlord risk management platform. He’s also an active real estate investor in Calgary, founder of the Alberta Landlord Community (5,000+ members, the largest landlord-only Facebook group in the province), and co-owner of Everway Legal Support, an eviction and process serving business operating across Canada.

We covered a lot of ground — here are the highlights.

What’s happening in Alberta right now

Alberta has been a darling of Canadian real estate investors for good reason: no rent control, business-friendly legislation, and strong population growth. But the picture is getting more nuanced.

Mackenzie shared that new build starts have been strong across the province — but CMHC’s MLI Select lending requirements have tightened significantly. Projects that started two years ago are finishing now with different rules than they were underwritten under. Developers are being asked to put in an additional $50,000 to $150,000 per deal at closing. And with rents coming in below original projections, some of those developers are becoming motivated sellers.

My take: rather than starting a development from scratch, it may make more sense to buy a distressed MLI Select project from a motivated seller — at a discount — than to go through the full development process yourself. The hard work is already done.

Calgary is also facing a new wrinkle: the city is reversing its blanket rezoning policy, making it harder to get permits on missing middle infill development. Mackenzie pointed out that even under the old blanket zoning, only about 15–25% of available properties actually pencilled out once you applied all the real constraints — lot size, setbacks, square footage minimums, and economics. The political backlash against densification is real, but the actual impact on supply is often misunderstood.

ATB’s latest GDP forecast for Alberta was revised upward — partly because of elevated global oil prices tied to the Strait of Hormuz situation. If you’re invested in Alberta real estate or Canadian energy, that’s a tailwind worth watching.

The SingleKey product suite — what landlords actually need

If you’re a landlord in Canada and you’re not using some form of tenant screening software, you’re taking on unnecessary risk. Mackenzie walked through everything SingleKey offers:

Tenant screening

SingleKey connects directly with Equifax and TransUnion for credit checks, searches the RCMP serious offender and sex offender database, pulls eviction data from provinces that make it available online, and cross-references with OpenRoom — a crowdsourced eviction database where landlords upload their LTB judgments. Everything runs from one application. No re-entering data, no manual credit check requests.

One feature I particularly like: SingleKey generates a shareable QR code for each rental listing. A serious tenant can scan it at the showing and complete the full application on their phone in the living room. The days of paper clipboards aren’t missed.

Tenant insurance

SingleKey can send a tenant an insurance invite at any point — new tenancy, existing tenancy, month-to-month. If the tenant uses SingleKey’s provider (through Walnut), you can mandate a minimum $2 million liability policy that the tenant cannot remove. And critically: if that policy is ever cancelled, you get automatically notified. You won’t know why — privacy prevents that — but you’ll know it happened, and you can get ahead of it before things go sideways.

Rent collection

Both pre-authorized debit (automated pull, slower — up to five to seven business days) and interactive e-transfer (faster, tenant-initiated) are available. Pros and cons to each, but both reduce the friction of chasing rent every month.

Digital lease signing

Now available across Canada (except Quebec and Nova Scotia, which require government-issued leases). You can embed conditions directly into the signing flow — including making tenant insurance a mandatory step before the tenant can sign the lease. That’s a powerful way to set the right foundation from day one.

The biggest new feature: AI-powered automated reference checks

This was the highlight of the episode — and we did a live demo on the show.

Mackenzie shared a stat that floored me: in a survey of landlords, 76% said they receive reference check calls from other landlords less than 10% of the time. I’ve always called references on every single tenant. Mackenzie does too. We’re apparently in the 1%.

The reason most landlords don’t do it: it’s awkward, time-consuming, and doesn’t scale. Getting through to someone, leaving voicemails, following up — it can eat 40 minutes of your day per application. Multiply that across multiple applicants and it’s a real problem.

SingleKey has been running an AI voice agent that automates this entire process. After 400 test calls, it’s achieving an 88% completion rate on full reference interviews. The agent calls the previous landlord, asks a structured set of open-ended questions — lease term, rental amount, payment history, pets, lease breaches, criminal record, and the key one: would you rent to this person again? — and delivers a PDF summary plus the full call recording.

The open-ended question format matters. If you just ask “was this a good tenant?”, you’re cueing up a yes/no that a fake reference can easily fake. When you ask “what was the rental amount?”, “when exactly did the tenancy start and end?”, and “can you describe the pets?” — you’re requiring the reference to have actual knowledge of the tenancy. A fake reference usually doesn’t.

We actually ran a live demo during the episode. I answered as a previous landlord for a fictional tenant named “John Tennant” at 123 Sesame Street, Edmonton, Alberta. The AI handled an incomplete address, asked follow-up questions, adapted to my answers in real time, and wrapped up the full interview in under two minutes. It was genuinely impressive.

Mackenzie’s point on the broader picture: this isn’t automating a job someone was doing — 76% of landlords weren’t doing it at all. This is adding a layer of due diligence that simply didn’t exist before, at a cost and time commitment that makes it viable at scale.

Vacancy rates and what they mean for Ontario landlords

Vacancy rates are rising across Ontario. Mackenzie noted they’re being reported at around 5% in some markets, and likely higher given data lag. Part of the reason: properties that were listed for sale are now coming back onto the rental market as sellers can’t find buyers at the prices they need. More rental supply means more competition for tenants — which is good for renters and harder for landlords.

For Ontario landlords specifically, the lesson is clear: tenant quality matters more than ever. A vacant unit is painful. A bad tenant in Ontario — where LTB timelines can stretch six months or more — is potentially catastrophic. Tools like SingleKey aren’t a nice-to-have anymore. They’re part of operating responsibly.

Bottom line

Canadian real estate is getting more complex. CMHC is tighter. Rents are softer in some markets. Vacancy is rising in Ontario. And fraudulent rental applications are getting easier to fake with AI tools — which makes verified, third-party screening even more important.

SingleKey’s suite — credit checks, eviction searches, insurance, digital leases, rent collection, and now automated AI reference checks — is the most comprehensive landlord toolkit I’ve seen in Canada. If you own rental properties, there’s no reason not to have a free account.

Want to stay ahead of what’s happening in real estate and the economy? 

Subscribe free at www.truthaboutrealestateinvesting.ca — get new episodes delivered straight to your inbox. 

Thinking about your next move as a real estate investor? 

Book a free strategy call with the iWIN team: Apply here

Subscribe to The Truth About Real Estate Investing for Canadians — ranked #81 business podcast on iTunes. 

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/ontario-landlord-horror-story-7-months-no-rent-vs-albertas/id1100488294?i=1000762395164

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/Ontario-Landlord-Horror-Story-7-Months-No-Rent-vs-Albertas-30-Day-Eviction-e3i2lqu 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/215551c4-6f72-4715-81fb-34cf6084cef7/the-truth-about-real-estate-investing-for-canadians-ontario-landlord-horror-story-7-months-no-rent-vs-alberta%27s-30-day-eviction

Audible: https://www.audible.ca/pd/B0GXW87LXN?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/fcsdT3DM7XI

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Recorded: March 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Rachel Oliver

Rachel Oliver has been in rent-to-own since 2010. She and her husband Neil have run one of the only dedicated rent-to-own companies in Canada — operating in Ontario and Alberta — and they have helped nearly 1,000 families get into home ownership. 

She has also watched most of her competition disappear. 

The market downturn did not just slow rent-to-own down. It broke the original model entirely. Rachel knows this better than anyone — because she built that model, saw it work spectacularly for years, and then watched it fail when the conditions changed. 

Her conclusion: Rent-to-Own 1.0 is retired. And what replaced it is worth paying attention to. 

Why Rachel Got Into This in the First Place 

Rachel’s entry into real estate investing was not strategic. It was survival. 

She was diagnosed with cancer during her first maternity leave. Already squeezed financially from being on mat leave, the year that followed — running from treatment to treatment, needing childcare for 50 percent of each day — drained the budget her husband had carefully built. His full-time income was not enough. 

What saved them was the equity in their home. A small Ajax house they had bought from Tridel builder. By the time they took occupancy, the value had already climbed from where they signed. That equity let them stay on top of their bills and rebuild. 

“I took that away and realized there are so many families that struggle through their personal setbacks — and if you do not have the stability of home ownership, it is really hard to rebound.” 

That is the mission Rachel and Neil have been on ever since. Not just building wealth — enabling other families to have the same stability she had when she needed it most. 

The Rent-to-Own Model — What It Was 

The original model was straightforward. An investor buys a property. A future homeowner moves in, pays a monthly amount that covers the carrying costs plus a forced savings component called an option credit. At the end of a set term — typically four years — the future owner exits by purchasing the property at a pre-agreed price. 

In a rising market, it worked beautifully. The pre-set exit price, typically based on 4 percent annualized appreciation, was usually below what the property was actually worth by exit. Tenants walked away with equity. Investors collected passive cash flow and a capital gain. Almost nobody had a losing scenario. 

Then the market reversed. 

Why 1.0 Failed 

Two things broke at the same time. First, COVID changed tenant behaviour. The option credit — the forced savings portion stacked on top of rent — is optional in a legal sense. When financial stress hit, tenants stopped paying it. Without enough saved for a down payment, they could not qualify to close. 

Second, valuations stopped cooperating. In roughly 50 percent of markets in 2022 and 2023, properties were appraised below the exit price that had been set years earlier using historical growth rates. Tenants who could afford to close did not want to. They were being asked to pay above market value. 

“Rent-to-Own falls apart when the tenant looks at the exit price and says — you set me up in a deal where I am overpaying for a property.” 

Rachel is not defensive about it. The prices were set with the best intentions and the historical data to back it. The market just did not cooperate. The honest answer is that a model built on a locked-in future price has a structural weakness when appreciation stops. 

She extended deals and, negotiated splits — tenant pays an extra $10,000, investor drops by $10,000. She also found the workarounds. But she also recognized that workarounds are not a business model. 

🎙️ Listen to the full podcast

Rent-to-Own 2.0: What Changed 

The locked-in exit price is gone. That is the core change. 

In Rent-to-Own 2.0, the future owner and investor enter an equity sharing arrangement. The future owner comes in with a 5 percent down payment — on a $630,000 property that is $31,500 of their capital offsetting the investor’s out-of-pocket costs, bringing effective loan-to-value to 85 percent. They pay the carrying costs each month. At exit, the property is appraised at fair market value. Both parties share in the outcome. 

The investor gets the lion’s share because they carry the mortgage and the title. The future owner gets a proportionate share based on how much they brought into the deal. The more capital they commit, the more negotiating power they have on the equity split. 

The deal Rachel walked through on air: a four-bedroom, three-bathroom renovated home in Orangeville, purchased at $630,000 at a 5.34 percent interest rate. Cash flow to the investor after all expenses: $800 per month from day one. 

“Where are you getting double-digit returns with $800 monthly cash flow in a flat market? I will do those deals all day long.” 

If the property stays flat over four years, the investor still earns a double-digit annualized return from cash flow and mortgage pay-down alone. If values climb by 5 percent, that $31,500 initial contribution from the future owner grows to approximately $50,000 — a meaningful outcome for a family that could not otherwise access the market. 

What Makes the Tenant Different 

Rachel’s most compelling argument for rent-to-own as a passive investment strategy is the tenant profile. These are not renters. They are future owners with real money in the deal. 

Out of roughly 75 to 80 live deals during the most turbulent period of COVID, Rachel had one non-payment that dragged to an eight-month eviction process. One. The rest negotiated, adjusted, and stayed invested in their outcome. 

The property maintenance responsibility sits entirely with the future owner. No landlord calls. No repairs billed to the investor. The investor holds title, collects cash flow, and waits for the exit. 

Rachel’s framing: if your goal is passive income with low headache and a tenant who behaves like an owner — this is the structure that gets you there. 

Who This Strategy Is For 

Rachel is clear that rent-to-own in any form is not for everyone. You need to qualify for an investment property mortgage at 20 percent down. You need to be comfortable with a multi-year hold. And you need to stop comparing today’s market to what it looked like five years ago. 

She made this point directly: investors who have never been through the boom years tend to be more optimistic about what today offers. Investors who lived through 2021 are still lamenting what they lost. The ones getting deals done right now are the ones who decided to stop comparing. 

“You cannot have it both ways. You cannot have aggressive appreciation and low prices and low interest rates all at once.” 

Rachel’s own portfolio has declined in net worth on paper. She is not hiding from that. But she is also cash flowing, carrying land-based properties that she can sell when she needs to, and building a business that has now survived 16 years of every kind of market cycle. 

Final Thought 

Rachel closed with a quote that stuck: “Look where the puck is going versus cranking your neck to see where it was before. Even if it seems like the puck is not going in the right direction — eventually you will score a goal.” 

The families still waiting on the sideline for the market they remember are waiting for something that is not coming back. The ones getting into homes today — through Rent-to-Own 2.0 or otherwise — are building equity while everyone else waits. 

Thinking about your next move as a real estate investor? 

Book a free strategy call with the iWIN team: Apply here

Subscribe to The Truth About Real Estate Investing for Canadians — ranked #81 business podcast on iTunes. 

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/rent-to-own-1-0-is-dead-here-is-what-replaced-it/id1100488294?i=1000759766412

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/Rent-to-Own-1-0-Is-Dead–Here-Is-What-Replaced-It-e3hgaat 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/6aba9d28-d87a-4286-9d79-c0112a7dbd8a/the-truth-about-real-estate-investing-for-canadians-rent-to-own-1-0-is-dead-here-is-what-replaced-it

Audible: https://www.audible.ca/pd/B0GW8JNWDG?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/T4BPVqWzREI

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Recorded: March 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Andy Tran

Andy Tran has been building things in Ontario for over a decade. He’s done basement conversions, garden suites, a 60-unit student residence in Hamilton he eventually sold, and everything in between. 

His conclusion after all of it: you don’t have to build big to do well. In fact, in 2026, the most powerful move available to Ontario investors might be the smallest one on the scale — the 4+1 or 6+1 unit build in Toronto. 

Andy calls it the sweet spot. Here’s why it works. 

The Problem With the Market Right Now 

New home sales in January 2026 hit their lowest level in roughly 30 years — around 270 sales. Housing starts are a lagging indicator, but the pipeline is nearly empty. Traditional builders aren’t moving because development charges make the numbers impossible. 

The result: a supply crunch is quietly building. Rents are soft now, but the math on what’s coming — especially in three to four years — is hard to argue with. 

“When you look at the last 25 years with real estate going up 7%, that’s in lockstep with money supply. It’s not going to be a straight line, but at some point it will pick back up.” 

The question isn’t whether to invest. It’s what to build, and where. 

Why 4+1 and 6+1 Are the Sweet Spot 

Ontario’s missing middle zoning changes opened the door to multi-unit builds on single-family lots — but not all unit counts are equal. Andy’s sweet spot is the 4+1 (four units plus a garden suite) and the 6+1 (six units plus one). 

The reason comes down to three advantages that stack on top of each other: 

• No development charges. Six-plus units are exempt from development charges — the single biggest cost that makes traditional development unworkable right now. 

• As-of-right construction. These builds qualify as-of-right, meaning no special city approvals, variances, or committee hearings. 

• Commercial financing. Five or more units opens access to MLI Select — CMHC’s commercial financing program with highly favorable terms. 

Ten-unit builds get the site plan approval exemption but lose the development charge exemption. For most mom-and-pop investors, Andy says four-plus-one or six-plus-one is the better trade-off. 

Why Toronto Specifically 

Andy makes the case for Toronto over Hamilton, Oshawa, or other secondary markets that many Ontario investors have used for the past decade. 

Toronto eliminated its floor space index (FSI), meaning you can build larger structures with minimal setbacks — reducing per-square-foot cost. The tenant profile is stronger: professional, higher income, lower conflict. And the city, despite all its bureaucratic quirks, is actively leading the missing middle push. 

The most compelling angle is for immigrant families. Andy’s strategy targets three-bedroom units near high-ranking schools in Etobicoke, Scarborough, and East York — exactly the product that isn’t being built anywhere else. 

“If you’re building three-bedroom units near a good elementary, middle, and high school — how valuable is that to an immigrant family that wants to settle and own?” 

An investor could build a six-unit building, condominiumize it, and sell individual units to families who want ownership but can’t afford a $1.2M townhouse. The Mortimer project in Toronto did exactly this, with units selling at $1M+ each in 2023. 

Who This Strategy Is For 

Andy breaks the investor pool into two groups: 

Equity builders — younger investors growing their net worth who are better off buying existing tenanted duplexes in secondary markets and accumulating. Don’t build — buy. 

Cashflow seekers — investors in their 50s and 60s who have equity, don’t want to sell in a down market, but want income. They have a big backyard or a property that can support a build. For them, adding a $300K garden suite to get $3,000/month in rent makes complete sense. 

The key is knowing which avatar you are before you act. 

How Passive Can This Be? 

Very — if you build the right team. 

Andy’s firm, Suite Additions, handles design and permitting. You find the property (or a realtor who understands missing middle), hire a Tarion-registered builder, and find a lender familiar with MLI Select. Andy’s office navigates the city so you don’t have to. 

“We take the beating from the city so you don’t have to.” 

For investors who want to go even more passive, there are GP/LP joint ventures and REITs now entering the missing middle space. The more hands-off, the lower the return — but the optionality exists. 

Andy also recommends downloading the Ontario Missing Middle Toolkit — a free 30-page guide his team built from scratch covering contractors, planners, financing, and city processes. Available at suiteadditions.com. https://creators.spotify.com/pod/profile/erwinszeto/episodes/Build-6-Units-in-Toronto-and-Pay-Zero-Development-Charges-e3gke47/a-acho5ab

🎧Listen to the full episode here

10 Questions Answered on Missing Middle Real Estate and Development in 2026 

1. What is the “sweet spot” for real estate development in Toronto? 

Andy Tran defines the “sweet spot” as building 4+1 or 6+1 units (four or six primary units plus a garden suite).These configurations are permitted “as of right” and are completely exempt from massive development charges. 

2. Why should investors avoid building 10-unit properties in Toronto? 

While 10-unit builds are exempt from lengthy site plan approvals, they lose the crucial development charge exemption. For small-to-medium investors, paying development charges on 10 units destroys the profitability of the project. 

3. Why is Toronto a better market for multi-unit builds than secondary cities? 

Toronto eliminated its floor space index (FSI), allowing developers to build larger structures with minimal setbacks. Additionally, the tenant profile in Toronto is typically stronger, professional, and lower-conflict compared to secondary markets. 

4. What type of housing is in the highest demand for new immigrant families? 

Immigrant families want ownership and space. They are looking for three-bedroom units near high-ranking schools in areas like Scarborough and East York. Because condo developers generally do not build three-bedroom suites, there is a massive supply gap. 

5. Can you sever and sell individual units in a 6+1 multiplex? 

Yes. Investors can build a six-unit building and “condominiumize” it—creating separate legal titles for each unit. These units can then be sold individually for $700,000 to $1,000,000 to families who cannot afford a traditional townhouse. 

6. Should young investors build garden suites to grow their equity? 

According to Andy, younger “equity builders” are usually better off buying existing, tenanted duplexes in secondary markets to accumulate wealth, rather than taking on the high capital costs and risks of new construction. 

7. Who benefits the most from adding a garden suite in 2026? 

“Cashflow seekers”—typically investors in their 50s and 60s who already have significant equity in their properties. They can invest approximately $300,000 to build a garden suite that yields $3,000 a month in steady rental incom. 

8. What is CMHC MLI Select financing, and is it hard to get? 

MLI Select offers highly favourable commercial financing with amortizations up to 45 or 50 years. However, CMHC is increasingly favouring new construction over conversions, and making it much harder to qualify unless strict accessibility and energy efficiency targets are met. 

9. Do you need to deal with the city to build a multiplex or garden suite? 

No. Investors can hire architectural design firms like Suite Additions to handle all the design, permitting, and municipal bureaucracy. They navigate the red tape and hand you a permit ready for a Tarion builder. 

10. How much capital is required to build a tear-down multiplex in Toronto? 

For a project that involves tearing down an old property and building a new multiplex with a garden suite, investors should expect capital requirements to range between $800,000 and $1.5 million. 

🎧Listen to the full episode here

Thinking about your next move as a real estate investor? 

Book a free strategy call with the iWIN team. Apply here.

Connect with Andy 

Andy Tran is the founder of Suite Additions, an architectural design firm specializing in missing middle housing across Ontario. 

Website: suiteadditions.com — including the free Ontario Missing Middle Toolkit 

YouTube: suiteadditions 

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/build-6-units-in-toronto-and-pay-zero-development-charges/id1100488294?i=1000755965117

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/Build-6-Units-in-Toronto-and-Pay-Zero-Development-Charges-e3gke47 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/cab94d83-557e-4615-a080-5605b05c8c40/the-truth-about-real-estate-investing-for-canadians-build-6-units-in-toronto-and-pay-zero-development-charges

Audible: https://www.audible.ca/pd/B0GSZYL4QT?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/gZw7xMmxqrI

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Recorded: March 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Glen Sutherland

For the last few years, many investors looked like geniuses simply by buying properties and riding the wave of massive market appreciation. But as the market shifts in 2026, the days of banking on property values going up 10% to 20% every single year to save a bad deal are over. 

If your U.S. real estate investment only works because you are counting on appreciation, you are gambling, not investing. 

This week on The Truth About Real Estate Investing for Canadians, I sit down with Glen Sutherland, a full-time real estate investor, educator, and host of the Canadian Investing in the U.S. podcast. 

For nearly a decade, Glen has helped Canadians break into U.S. real estate. From distressed single-family homes to large multifamily projects, Glen has built scalable systems that allow him to invest entirely remotely. In fact, he rarely even visits his properties in person! 

Here is how Glen is successfully navigating the 2026 market and how Canadians can legally and profitably invest south of the border. 

4 Key Takeaways from This Episode: 

1. Appreciation Is a Bonus, Not a Strategy 

Markets move in cycles. While some markets are currently showing signs of recovery and improving rent rates, relying on future appreciation in your deal analysis is a highly risky play right now. Instead, Glen focuses on markets where the numbers make sense from day one, driven by strong employment and high-paying jobs, like the aerospace and tech industries moving into Huntsville, Alabama. 

2. Force the Appreciation 

If you want to mitigate risk, you need to force the value of the property yourself. Glen’s core strategy involves buying highly distressed properties—the kind of properties that banks and realtors won’t even touch—renovating them, and then refinancing or flipping them. By doing the heavy lifting upfront, you manufacture your own equity. 

3. Remote Investing Requires Ruthless Systems 

You don’t need to cross the border to be a successful U.S. investor, but you do need bulletproof systems. Glen operates his entire business from Canada using detailed Standard Operating Procedures (SOPs), virtual assistants, and strict checklists. His biggest piece of advice? Redundancy. Always have two property managers and multiple contractors available in any city you invest in, because life happens, and you don’t want to be left stranded when a team member leaves. 

4. The Power of “Subject-To” Investing 

The U.S. offers creative deal structures that are simply unavailable or highly restricted in Canada. One of Glen’s favorite strategies is “Subject-To” (Sub2) investing, where you take over an American’s existing mortgage, allowing you to secure incredibly cheap, locked-in interest rates while taking over the deed to the property. 

If you are a Canadian investor looking to escape low yields and difficult tenancy laws by diversifying into the U.S. market, you need to hear this episode. 

🎧Listen to the full podcast

You can learn more about Glen Sutherland and his coaching program at www.canadianinvestingintheusa.com. 

10 Real Estate Questions Answered in This Episode 

1. Is appreciation a reliable real estate investing strategy in 2026? 

No. Glen warns that if you need appreciation to make your deal numbers work, it is far too risky in today’s market. Appreciation should always be treated as a bonus, not a requirement. 

2. What is forced appreciation in real estate investing? 

Forced appreciation means proactively increasing a property’s value rather than waiting for the market to go up. Glen does this by purchasing heavily distressed properties at a massive discount, fully renovating them, and then refinancing based on the new, higher value. 

3. Can Canadians invest in U.S. real estate without visiting the properties? 

Absolutely. Glen often goes through the entire purchase, renovation, and sale process without ever physically stepping foot on the property. This is achieved by building a strong local team of property managers and contractors, and managing them through strict checklists and systems. 

4. What is a “Subject-To” (Sub2) real estate deal? 

Subject-To investing is a creative financing strategy popular in the U.S. where an investor takes over the deed of a property while leaving the seller’s original mortgage in place. This allows the investor to capitalize on the seller’s extremely low, previously locked-in interest rate. 

5. Why is redundancy important in remote real estate investing? 

In real estate, you are highly dependent on people (contractors, property managers, etc.). If your sole contractor quits or goes out of business, your project stalls. Glen recommends building redundancy—having backup property managers and multiple contractors—in every market you invest in to protect your business. 

6. Do you need a U.S. Social Security Number or Visa to invest in the U.S.? 

No. While having an E2 Visa, a U.S. driver’s license, or an SSN can be helpful for certain types of U.S. bank lending or tax structures, you do not strictly need any of them to begin investing and buying property in the United States. 

7. Why do some investors prefer large multifamily buildings over single-family homes? 

Multifamily buildings offer powerful economies of scale. Instead of dealing with multiple property managers across scattered single-family homes, you can manage 100 units under one roof, standardize all the paint and materials, and dramatically increase the building’s value simply by raising rents slightly across the board. 

8. What is the biggest challenge of investing in large multifamily properties? 

The speed of money. While large multifamily deals can generate significant long-term wealth, the operators are typically paid last in the capital stack. Single-family homes allow for a much faster turnaround of your capital (e.g., 3 to 6 months) to generate quick income. 

9. How do virtual assistants (VAs) help real estate investors? 

VAs can manage repeatable tasks such as bookkeeping, uploading podcasts, or running deal analysis spreadsheets based on standard operating procedures (SOPs). This frees up the investor’s time to focus on high-level strategy and acquisitions. 

10. What is the biggest regret of aspiring real estate investors? 

According to Glen, the biggest regret new students have is that they waited too long to start. Many realize they could have quit their jobs years ago if they had just taken action earlier instead of sitting on the sidelines. 

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/how-canadians-can-win-in-u-s-real-estate-in-2026-without/id1100488294?i=1000753354383

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/How-Canadians-Can-Win-in-U-S–Real-Estate-in-2026-Without-Betting-on-Appreciation-e3fu2lc 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/4636ffa0-a58c-40ed-a1ac-b5855504419e/the-truth-about-real-estate-investing-for-canadians-how-canadians-can-win-in-u-s-real-estate-in-2026-without-betting-on-appreciat

YouTube: https://youtu.be/KEjIDSWjmEY

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Recorded: February 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Adam Kitchener

Folks, welcome back to the show. 

It is every real estate investor’s nightmare. You follow the rules, use the BRRRR strategy. Build a portfolio worth over $14 million. And eventually, you achieve what looks like financial freedom. 

And then, while you are on vacation in Thailand, your debit card stops working. 

You call the bank, and they tell you: The CRA has frozen everything. 

This week on The Truth About Real Estate Investing for Canadians, I sat down with Adam Kitchener. If you’ve been around the Hamilton/Ontario investing scene, you likely know Adam. He started investing in 2016, built a massive portfolio, and ran a property management company. 

But for the last three years, Adam has been fighting a war with the CRA that cost him almost everything. 

The Audit That Spiraled 

Adam shares the harrowing details of how a routine audit turned into a financial death spiral. It wasn’t about fraud or tax evasion. It started with simple misunderstandings, auditors asking why he didn’t charge HST on residential rent (you don’t) or asking if he had a cash register for his rental business. 

Despite having meticulous records, the CRA froze his personal accounts. Because he had personally guaranteed his mortgages (a common practice for investors scaling up), the banks saw the CRA judgment and pulled his funding. 

The “Asset Rich” Trap We talk a lot about being “Asset Rich, Cash Poor.” Adam’s story is the extreme version of this. He had millions in equity, but when the CRA froze his liquidity, he couldn’t service the debt or pay his contractors. 

He was forced to surrender properties to the bank to avoid further legal battles. He went from managing a $14M portfolio to working three jobs just to pay back his contractors, because Adam is a man of integrity who refused to let his tradespeople suffer for his tax battle. 

The Mental Toll I want to thank Adam for his vulnerability in this episode. He opens up about the darkness of losing his identity as a “successful investor.” He discusses the mental health toll, the suicidal thoughts, and the moment he realized that his net worth did not define his self-worth. 

The Rebuild: Renovation Solutions Adam is still standing. He realized that the “hustle” of property management and massive portfolios wasn’t the only way. He has returned to his roots, launching Renovation Solutions, a contracting business focused on helping other investors turn units over efficiently. He’s rebuilding, but this time with a focus on simplicity and bulletproof corporate structure. 

🎧 Listen to the full episode here

10 Real Estate Tax & Legal Questions Answered in This Episode 

1. Can the CRA freeze my bank account without notice?

Yes. Adam discovered his accounts were frozen only when his debit card was declined while on vacation in Thailand. The CRA stated they had sent a letter, but because he was traveling, he did not receive it in time to respond. 

2. Do landlords have to charge HST on residential rent in Ontario? 

No. Long-term residential rent is exempt from HST. However, Adam shares a story of an auditor specifically asking why he wasn’t charging HST on his rental income, highlighting the importance of having a knowledgeable accountant to defend you against auditor errors. 

3. What happens to my mortgages if the CRA sues me? 

If you have personally guaranteed your corporate mortgages (which is common for real estate investors), a CRA judgment against you personally can trigger a “default” clause with your lenders. Adam’s lenders called his mortgages not because he missed payments, but because of the CRA judgment. 

4. What is “Audit Insurance” and do investors need it? 

Audit insurance covers the professional fees (accountants and lawyers) required to defend you during an audit. Adam notes that defending himself cost thousands of dollars he didn’t have access to because his accounts were frozen. Having this insurance can prevent you from running out of cash during a dispute. 

5. Can a general accountant handle a complex real estate audit?

Adam advises against using a generalist. He stuck with a “good guy” accountant too long, but when the complex audit hit, the workload was overwhelming. He recommends upgrading to a specialist firm before you think you need one. 

6. How does “Separation of Church and State” apply to real estate assets?

Adam emphasizes the need to completely separate personal assets from business assets. Because he had assets in his personal name (and personal guarantees), the CRA was able to seize/freeze personal funds that strangled his business operations. Proper corporate structuring creates a firewall. 

7. Why would a bank call a mortgage if I’m making payments? 

Even if you have never missed a mortgage payment (as Adam hadn’t), lenders monitor your credit and legal standing. A substantial tax lien or judgment effectively kills your creditworthiness, causing lenders to view you as high-risk and call the loan. 

8. Is property management a scalable business model? 

Adam built a large property management company but found it difficult to scale profitably due to the high volume of “bosses” (landlords) and tenants. He eventually closed it to focus on his own portfolio, noting it is a tough, low-margin industry. 

9. What triggers a CRA audit for investors? 

While sometimes random, Adam suspects his audit was triggered by a discrepancy between a year of low taxable income (due to write-offs) followed by a year of high asset acquisition (refinancing). The CRA looks for lifestyle spend that doesn’t match reported income. 

10. How long does a CRA audit take? 

Adam has been dealing with this for three years. It is not a quick process. He warns that investors need the stamina and liquidity to survive a multi-year battle, as the CRA can move very slowly while your assets remain frozen. 

🎧 Listen to the full episode here

As always, thanks for listening (all 17 of you!), and keep hustling. If you’re not already on my free email list, you can join at: 

👉 www.truthaboutrealestateinvesting.ca 

(Add your name and email on the right-hand side.) 

That’s how you’ll hear about new episodes, webinars, and live events like the Wealth Summit, where in-person seats sold out in a week. 

Being on the list helps you avoid disappointment. More importantly, it helps you avoid financial losses and fraud. We’ve seen this with Fortress Developments, Epic Alliance, and others currently in hot water with the Ontario Securities Commission. Cons and frauds share common patterns, and learning to spot them early matters. 

---

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/how-a-%2414-million-portfolio-evaporated-the/id1100488294?i=1000749289818

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/How-a-14-Million-Portfolio-Evaporated-The-Adam-Kitchener-Story-e3ev1rq/a-acfg7bj  

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/a4641340-9cf8-466e-b59c-cff04e429c6e/the-truth-about-real-estate-investing-for-canadians-how-a-14-million-portfolio-evaporated-the-adam-kitchener-story

Audible: https://www.audible.ca/pd/B0GMY9X9W1?source_code=ASSGB149080119000H&share_location=pdp 

YouTube: https://youtu.be/I_GmtpWkkpU

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Recorded: January 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Winnie Tsang, Former CFO

Folks, welcome back to the show. 

If you’ve been listening to me for a while, you know I am a die-hard real estate guy. I’ve built an 8-figure portfolio, I’ve been a landlord for 20 years, and I’ve coached hundreds of investors. 

But recently, I’ve been asking myself and my clients a hard question: Is the return on investment worth the return on hassle? 

I’m currently dealing with a broken washer that’s only three months old but costing me $300 to fix, plus a non-paying tenant. For high-energy entrepreneurs, active real estate is still a goldmine. But for me, with a young family, I want my investments to be boring, passive, and profitable. 

That is why I brought Winnie Tsang on the show. Winnie is a former corporate CFO for massive companies like Rogers and Accenture who made a pivot. She’s now a partner at Open Concept Financial Group, acting as a “Personal CFO” for families. 

We talk about “financial jujitsu”—strategies like leveraged segregated funds and corporate-owned life insurance that allow you to build wealth without unclogging a single toilet. 

If you are sitting on retained earnings in your corporation or you’re tired of being a landlord, you need to read this. 

🎧 Listen to the full episode here

10 Money Questions Answered in This Episode (That Your Bank Won’t Tell You) 

1. Why are everyday investors diversifying away from local real estate? It’s about income diversification and resilience. Winnie notes that for many, real estate has turned cash-flow negative. By diversifying into other asset classes, you gain liquidity and options—allowing you to buy time, which is the only non-renewable resource.

2. What is the “Corporate Owned Life Insurance” tax hack? This is a game-changer for business owners (doctors, realtors, consultants). Instead of investing retained earnings in GICs (taxed at ~50%), you buy a whole life policy inside the corp. The death benefit eventually pays out to your shareholders (family) tax-free via the Capital Dividend Account. It transfers business wealth to personal wealth with massive tax efficiency. 

3. Why do people choose “inaction” when it comes to their wealth? Fear and a lack of clarity. Winnie explains that people often feel overwhelmed by choices (the “burden of choice”), so they do nothing. But inaction is a choice with consequences. A good plan gives you the clarity to make a move. 

4. What are “Leveraged Segregated Funds”? This is the strategy I wish I started 10 years ago. It involves using a smaller amount of cash (e.g., $2,500) to access a much larger loan (e.g., $50,000) to invest in the market. Because it’s a segregated fund, it often comes with downside protection, and the interest on the loan is tax-deductible. It amplifies the upside, similar to a mortgage on a house, but without the tenants. 

5. Why leave a high-paying Corporate CFO job to help families? Winnie spent years maximizing shareholder value for big companies, but the pandemic made her rethink her purpose. She realized that regardless of wealth level, families struggle with financial management, especially as they age. She wanted to apply that high-level strategy to everyday people. 

6. Why is an independent financial firm better than a bank advisor? No quotas. Winnie notes that independent firms don’t have to push “Product X” just because it’s the flavor of the month. They can assemble a bespoke solution using the best products from multiple institutions to actually serve the client’s goal, not the bank’s sales target. 

7. Is real estate actually “passive” income? No. We discuss how real estate is actually an active business, not a passive investment. True passive investing shouldn’t add stress to your life or take time away from your family. If you have to manage a property manager, it’s still work. 

8. Why is Estate Planning the most overlooked aspect of wealth? We avoid talking about death, but it’s the one certainty. Winnie points out that insurance is bought with your health and age; if you wait until you retire to plan your estate, it’s often too expensive or too late. Optimizing this early creates an exponential curve of growth for your legacy. 

9. How do cognitive biases hurt our investment returns? We suffer from “familiarity bias”—we buy real estate because our parents did, or because we made money on it once before. But doing the same thing when market conditions have changed (like high interest rates) leads to losses. You have to look at the objective data, not just what feels comfortable. 

10. What is the “Financial Jujitsu” approach? It’s about finding joy in figuring out how to make more money, work less, and pay less tax. It’s using the rules of the system (like the Capital Dividend Account or leverage) to maximize your returns with the least amount of effort. 

🎧 Listen to the full episode here

My Final Thoughts 

Folks, life is short. I want to spend my weekends with my kids, making slime and listening to Taylor Swift (don’t ask), not chasing rent payments. 

Real estate is a fantastic way to build wealth, but it isn’t the only way. If you are ready to look at your wealth holistically—insurance, investments, and estate planning—reach out to us. 

If you want to meet Winnie and hear more about these strategies, come to our Wealth Summit 2025. She’ll be there, and trust me, she’s way smarter than I am. 

Save the date

Wealth Summit 2026 · Hybrid (In-Person + Online) | Saturday, January 31st · 9:00 AM EST

Ready to make 2026 your smartest financial year yet? Join us for Wealth Summit 2026, where real estate, tax, and wealth-planning experts break down the proven blueprint for protecting and multiplying your wealth.

REGISTER HERE

Early-bird registration is now open — save 40% when you secure your spot early. Seats for the in-person experience are limited and always sell out fast.

Discover the frameworks, tax strategies, and legacy tools top performers use to stay ahead — no matter the market.

---

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/from-corporate-cfo-to-personal-cfo-a-2026-new-year/id1100488294?i=1000747020836

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/From-Corporate-CFO-to-Personal-CFO-A-2026-New-Year-Wealth-Reset-for-Investors-e3eaa92

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/ae98b6ad-0ce8-463d-b88d-1c2bb2939ecc/the-truth-about-real-estate-investing-for-canadians-from-corporate-cfo-to-personal-cfo-a-2026-new-year-wealth-reset-for-investors

Audible: https://www.audible.ca/pd/B0GK9ZJS13?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/T-ULjlsjqrI

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Recorded: January 2026

Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Guest: Mike Rosehart, Real Estate Analyst and Investor

Welcome back to the show. We had a returning guest on, and honestly, if you’re looking for a masterclass on how to pivot when the market punches you in the face, this is it. 

Mike Rosehart is back, and he’s not just doing student rentals in London anymore. We’re talking about a massive shift. He’s acquired a couple of hundred units in the last 12 to 18 months, pushing his portfolio north of $50 million. 

But it wasn’t a straight line up. We get into the messy stuff—the private lending deals that went south, the foreclosures, and how he turned those disasters into a goldmine in the hospitality space. Mike openly shares the challenges, admitting he had lending deals where borrowers stopped paying for 11 months and he waited too long to take legal action. 

If you are serious about scaling or you’re stuck trying to make the numbers work in this high-interest environment, you need to pay attention to the “Hotel to Apartment” conversion strategy Mike breaks down. It is absolute fire. 

🎧 Listen to the full episode here

10 Real Estate Questions Answered in This Episode 

1. Why are smart investors pivoting from residential rentals to hotels and motels? 

The margins in residential multifamily are tight right now. Mike explains that in markets like Ontario, you might pay $180,000 to $200,000 per door for a multifamily unit. However, you can buy a hotel or motel for $60,000 to $70,000 per key. That is half or a third of the cost for the same physical square footage, offering a massive arbitrage opportunity. 

2. Can you convert a motel into a long-term residential apartment? 

Yes, and it’s a massive value to add. Mike notes that many motels already have kitchenettes or the infrastructure for them. By spending $10,000 to $15,000 per unit on renovations and getting a simple change of use zoning (often around $5,000), you can convert them into residential apartments that qualify for CMHC financing. 

3. What are the dangers of private lending in a correcting market?

We talk about the ugly side of lending. Mike shares how he had lending deals go sideways where he was in a second mortgage position during a market correction. The lesson? If you are in a second or third mortgage position or holding a promissory note, your capital might be worthless because the first mortgage and legal fees eat up all the equity. 

4. How do you automate a hotel operation to slash costs? 

Mike isn’t running these like it’s 1990. He fires the expensive staff and cuts the franchise flags immediately. He uses AI bots for front desk operations, automated digital locks with codes that expire, and independent contractors for cleaning. This cuts costs by 50% compared to traditional operators. 

5. Why would an investor buy a property in cash right now? 

While leverage is king, cash is speed. Mike recently bought a 50-unit property in Sarnia (The Village Inn) with cash because lender fees were too high and the timeline was too tight for environmental assessments and appraisals. The goal isn’t to stay in cash, but to secure the deal, stabilize it over 6-12 months, and then refinance to pull the capital back out. 

6. How does the “Lifetime Capital Gains Exemption” apply to hotels? 

This is a huge tax nugget. Because hotels are considered “active businesses” rather than passive rentals, you can potentially utilize the Lifetime Capital Gains Exemption (LCGE) when you sell the shares of the corporation. If structured correctly with a family trust, you could shelter millions in profit tax-free,. 

7. Is it easier to evict a non-paying guest in a hotel vs. a tenant?  

Mike highlights that in a hotel/motel environment, if a guest doesn’t pay, you can simply disable their door code or call the police for removal. You avoid the 8-11 month delays typical of the Landlord and Tenant Board (LTB) in Ontario. 

8. What should you look for when taking over a distressed property? 

You want absentee owners or tired operators. Mike bought a hotel from a 92-year-old operator who had zero online presence—no Booking.com, no Expedia, just a phone number. By simply modernizing the marketing and operations, the revenue lift is instant. 

9. Is the BRRRR method still alive in Ontario? 

It is, but you have to buy deep. Mike mentions that detached houses in London, Ontario, have fallen significantly—sometimes trading at half of what they were in 2022. If you can buy a detached house for land value (e.g., $240k), add a unit, and create a duplex, the numbers start to make sense again. 

10. Is real estate investing scalable without a massive team? 

Mike argues that bigger deals are actually easier to scale than small ones. He puts a “mentee” or operating partner into his larger hotel deals to live on-site and manage operations in exchange for equity. This allows him to scale to hundreds of units without personally managing every toilet fix. 

🎧 Listen to the full episode here

My Final Thoughts 

Folks, the market has changed. What worked in 2017 isn’t working today. You can’t just buy a pre-con condo and hope it goes up. You have to force appreciation. 

Mike is showing us that there is opportunity in the ashes of this correction. Whether it’s buying distressed notes, taking over foreclosures, or converting motels into housing, the deals are there for the people willing to do the work. He’s proving that “active business” income is the new path to cash flow in 2025. 

If you want to see what Mike is up to, check him out on Instagram at @mikerosheart or search for The Village Inn Sarnia to see his latest project. 

Save the date

Wealth Summit 2026 · Hybrid (In-Person + Online) | Saturday, January 31st · 9:00 AM EST

Ready to make 2026 your smartest financial year yet? Join us for Wealth Summit 2026, where real estate, tax, and wealth-planning experts break down the proven blueprint for protecting and multiplying your wealth.

REGISTER HERE

Early-bird registration is now open — save 40% when you secure your spot early. Seats for the in-person experience are limited and always sell out fast.

Discover the frameworks, tax strategies, and legacy tools top performers use to stay ahead — no matter the market.

---

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/from-houses-to-hotels-a-real-life-monopoly-story/id1100488294?i=1000745436200

On Spotify: https://open.spotify.com/episode/48ISuXhSJMguNaxK3d6Edy?si=bDedAZnXS3iQ9FyBP82CVw

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/4b07e204-26bd-4242-8876-87dbaebb0c40/the-truth-about-real-estate-investing-for-canadians-from-houses-to-hotels-a-real-life-monopoly-story

Audible: https://www.audible.ca/pd/B0GH8LCLTB?source_code=ASSGB149080119000H&share_location=pdp

YouTube:https://youtu.be/5slXpuy5YV8

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Recorded: December 2025
Guest:️ Tim Hong, Property Manager specializing in selling and managing tenant-occupied properties.
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Selling an investment property in Ontario in 2026 is not the same game it was in 2021.

If you’re an investor in markets like Hamilton, Kitchener–Waterloo, or the GTA, you’re facing more listings, tougher financing, and smarter buyers. At the same time, interest rates are still high enough to squeeze cash flow, and the Landlord and Tenant Board remains a risk you want to avoid at all costs. 

In a recent episode of The Truth About Real Estate Investing for Canadians, I sat down with veteran investor, realtor, and property manager Tim Hong to talk about exactly what’s happening on the ground — and what smart investors are doing instead of panicking.  

Inventory Is Up 50–60%… But Prices Are Range-Bound 

Tim started by pulling fresh stats from his core markets: 

• Kitchener–Waterloo: active listings are up from about 810 in November 2023 to roughly 1,296 today — a 60% jump. 

• Hamilton: inventory is up from ~1,410 to 2,078 active listings, a bit more than a 50% increase. 

That’s a huge shift in supply, yet prices haven’t completely collapsed. From the February 2022 peak, we’re still roughly 20–30% down, but for the last three years prices have mostly been range-bound, bouncing up and down within a band.  

The takeaway: 

• If you’re listing your property now, understand you’re competing in a crowded marketplace. 

• Buyers have time and options. Conditions are back. So are offers conditional on the sale of the buyer’s home. 

Power-of-Sale and Estate Sales Are Setting the Bar 

When I pulled comparables recently, I saw more power-of-sale and bank-owned listings than at any time since I became a realtor in 2010. I also saw a bank-owned Hamilton Mountain bungalow duplex that sold for around $1.2M at the peak get resold for roughly $720,000 after the bank took it back. 

That’s a 40%+ haircut. 

These types of listings — bank sales and estate sales — are often: 

• Aggressively priced to clear quickly. 

• Heavily influencing buyers’ expectations on what a “deal” looks like. 

If you’re a regular investor trying to sell a tenanted duplex, you’re competing against those numbers, whether you like it or not.

Why Single-Family Homes Sell Faster Than Duplexes Right Now

Tim sees a big difference between “obvious rental properties” and end-user homes: 

• Legal duplexes, triplexes, and vacant student rentals: 

• Investors are cautious. 

• Financing is tighter and interest rates are higher. 

• Offers are often below what sellers want. 

• Single-family homes for end users: 

• Bigger buyer pool. 

• Still seeing healthy activity and occasional multiple offers, depending on location and price. 

Investors have no sense of urgency right now. They’ll buy only if the numbers are compelling. That means if your exit strategy relies on another investor paying top dollar, you may need to adjust your expectations — or your strategy.  

Plan A vs Plan B: Sell or Re-Rent? 

For many of Tim’s clients, the starting plan was: 

1. Tenant leaves. 
2. Touch up the property. 
3. List it for sale. 

In several cases, the market response was underwhelming: little activity, weak offers, or no offers at all. 

At that point, Tim sits down with the investor and runs the numbers on Plan B: 

• What can this property realistically rent for with a proper tenant-screening process? 

• What does cash flow look like at today’s interest rate? 

• Are you willing to hold for another 3–5 years? 

Often, the investor decides that re-renting is the better financial move. 

In one case, an investor was set on selling a property with long-term tenants paying below-market rent. Once they saw the projected sale price and tax implications, they weren’t excited. 

Tim approached the tenants directly, explained the situation, and negotiated a new lease at a higher rent that was still below market. The result? 

• The investor kept the property. 

• Cash flow increased by about $560 per month. 

• The tenants gained security and avoided the uncertainty of a new owner.  

That’s the power of creative negotiation and treating selling as one option, not the only option. 

The Resilience of University Student Rentals 

While many asset classes are feeling pain, university-area student rentals have quietly been one of the most resilient strategies over the last decade. 

Why? 

• Enrollment tends to increase during economic downturns. 

• Universities have more stable, diversified demand than some private colleges that leaned heavily on international students. 

• Student rentals naturally build in tenant turnover every 2–3 years, letting landlords reset rents to market regularly. 

College-focused markets tied to international enrollment — think Conestoga and similar schools — have seen dramatic drops and oversupply. But university zones around schools like Waterloo, Laurier, McMaster, and others are still seeing strong demand from quality students who want clean, well-managed housing.  

Bill 60 and the Future of Selling Tenanted Properties 

We also talked about Bill 60 and what it could mean for investors: 

• Shorter timelines for non-payment of rent (N4 going from 14 days to 7). 

• Requirements for tenants to pay 50% of outstanding rent into the system if they want to raise maintenance issues at a hearing. 

• Possible relief from compensation requirements if you give 120 days’ notice to a tenant for a buyer’s own use. 

None of this is a magic fix. But it may tilt the playing field slightly back towards responsible landlords who follow the rules. 

The safer strategy remains the same: avoid the Landlord and Tenant Board completely by screening tenants properly, communicating clearly, and handling issues early. 

Tenant Screening: Why Tim Hasn’t Been to the LTB in Two Years 

Tim’s property management company hasn’t had to attend the LTB in two years. His process is simple but strict: 

• Use SingleKey for credit and application processing. 

• Use OpenRoom to check for existing court orders. 

• Verify employment, income, and current landlord through independent searches. 

• Watch how tenants communicate and follow instructions. 

If someone no-shows a viewing without notice, asks for four parking spots on a property with one, or can’t be bothered to read the ad, they’re disqualified. 

Is it harsh? Maybe. 

Is it effective? Definitely. 

If you want high-quality, long-term tenants who pay on time and treat your property like a home, you need to raise the bar. 

Should You Buy Vacant or Tenanted Right Now? 

Given longer vacancy times for new listings and the sheer number of options tenants have, Tim makes a point many investors miss: 

• If you’re buying locally and want a relatively hands-off experience, consider buying a property with a good, paying tenant in place at a fair rent — as long as you can verify their history and lease. 

• If you buy vacant, be prepared for two months (or more) of vacancy, plus screening, showings, and uncertainty. 

In today’s market, time is money, and two months of lost rent plus your own time and stress can eat up a lot of the “deal” you thought you were getting.  

🎧 Listen to the full episode here

Final Thoughts: Hold, Sell, or Pivot? 

If you own investment real estate in Ontario right now, you don’t need fear. You need a clear decision-making framework: 

1. Check your numbers honestly. Can you carry the property for another 3–5 years if you re-rent at realistic market rents? 

1. Know your asset. Is it a quality property in a solid location, or is it a weak property that only looked good in a spreadsheet? 

1. Understand your buyer. Are you selling to an end user or another investor? The strategy, staging, and pricing are different. 

1. Have a Plan B. If the right offer doesn’t come, be ready to re-rent, renegotiate with tenants, or refinance instead of selling at a painful discount. 

Save the date

How to Sell Investment Property for Maximum ROI. Online-Only Live Masterclass | Tuesday, January 13th · 8:00 PM EST

If you’re thinking about selling in 2026, join us on January 13th at 8 p.m. Eastern for our free IWIN training: “How to Sell an Investment Property for Maximum ROI.” 

REGISTER HERE

We’ll walk through: 

• Real examples of deals that sold vs. deals that pivoted to Plan B. 

• How to price properly in a market full of bank sales and estate sales. 

• Tenant strategies that make your property more attractive — or at least not a liability — when you hit MLS. 

In this market, you don’t have to get crushed. You just have to be smarter than the average seller. 

Wealth Summit 2026 · Hybrid (In-Person + Online) | Saturday, January 31st · 9:00 AM EST

Ready to make 2026 your smartest financial year yet? Join us for Wealth Summit 2026, where real estate, tax, and wealth-planning experts break down the proven blueprint for protecting and multiplying your wealth.

REGISTER HERE

Early-bird registration is now open — save 40% when you secure your spot early. Seats for the in-person experience are limited and always sell out fast.

Discover the frameworks, tax strategies, and legacy tools top performers use to stay ahead — no matter the market.

 

---

Top 10 FAQs About Selling Investment Properties in Ontario (2026 Edition) 

Q: How has the Ontario real estate market changed for investors going into 2026? 

A: Inventory in markets like Hamilton and Kitchener–Waterloo is up 50–60% compared to 2023, while prices are roughly 20–30% below the 2022 peak and range-bound, so investors face more competition when selling. 

Q: Is 2026 a good time to sell an investment property in Ontario? 

A: It can be, if you’ve owned for several years and price realistically against bank sales, estate sales, and higher inventory, but many investors are better off re-renting and waiting out the market if they don’t need to sell. 

Q: What’s the biggest mistake investors make when selling rental properties in Ontario? 

A: Hiring a non-investor realtor and ignoring tenant issues; when the property doesn’t sell, they pivot to Plan B with a poorly screened tenant and can end up in Landlord and Tenant Board nightmares. 

Q: Are student rentals still a good investment strategy for Canadian investors? 

A: University student rentals near major Ontario campuses remain one of the most resilient cash-flow strategies, thanks to strong enrollment and regular tenant turnover, whereas college-heavy markets reliant on international students have struggled. 

Q: How long does it take to find a good tenant in the 2026 Ontario rental market? 

A: In many areas it now takes 6–8 weeks or more to find a high-quality tenant for single-family homes, duplexes, and basement units, so investors should budget for at least two months of vacancy. 

Q: What are the best tenant screening tools for Ontario landlords? 

A: Many professional property managers use SingleKey for credit and application processing and OpenRoom to check for existing court orders, combined with manual checks of income, landlord references, and online searches. 

Q: How will Bill 60 impact landlords and selling investment properties? 

A: Bill 60 proposes shorter timelines for non-payment, potential changes to compensation when buyers move in, and rules requiring tenants to pay a portion of rent owed before raising maintenance complaints, which slightly improves the environment for responsible landlords. 

Q: Should I buy a vacant rental property or one with tenants in place? 

A: In today’s market, buying a property with a strong, paying tenant at near-market rent can be safer because buying vacant often means at least two months of vacancy and extra leasing risk. 

Q: What types of rental units are most in demand in Ontario right now? 

A: Larger, brighter units—especially above grade, with multiple parking spots and family-friendly layouts—are renting faster than small micro-condos or cramped basement apartments. 

Q: How can Canadian investors protect their cash flow until interest rates drop? 

A: Focus on tenant quality over speed, consider rent renegotiations with below-market tenants, and be willing to pivot from selling to re-renting if offers don’t match your long-term goals. 

---

📜 Full Transcript

The full, cleaned transcript of my conversation with Tim Hong is available here for anyone who wants to dive deeper.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/apartments-vs-business-income-how-real-estate-investing/id1100488294?i=1000733146751

On Spotify: https://open.spotify.com/episode/0g5Jt74Qff54WifcfEU6FH?si=3554156498454d05

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/c50ae533-1e20-4bf2-80d9-82ddb8d70b7d/the-truth-about-real-estate-investing-for-canadians-how-to-sell-a-tenanted-property-in-2026-what-investors-need-to-know-now

Audible: https://www.audible.ca/pd/B0G53GJWGW?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/-G3MkQjEH4Y

You’ve Built Wealth. Now It’s Time to Understand It. 

You’ve Built Wealth. Now It’s Time to Understand It. 

After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.” 

Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live. 

Download your free Wealth Freedom Blueprint 

Final Thoughts

Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life. 

That’s what iWIN Wealth Planning is here for. 

This is how we’re creating predictable, stress-free wealth for Canadian families… 
so you can enjoy the life you’re building. 

Book your Wealth Planning Call 

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Recorded: November 2025
Guest:️ Chelsey Fawcett, OREIO President and Founder of Grant Solutions Canada 
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Affordable rental development in Canada is tough: land and trades are expensive, and rents can’t float to infinity. Grants—federal, provincial, municipal—and targeted credits can bridge the gap. In this episode, OREIO President and Grant Solutions Canada founder Chelsey Fawcett explains how developers build grantable projects, why many funds prefer build-and-hold rentals, and how manufacturing/employment grants support prefab and tiny-home production that lowers costs and speeds delivery. 

Key Takeaways: 

• Grants fund solutions to public problems. Today’s problem is affordability; projects that reserve a share of units below local medians score higher and can unlock forgivable loan components. Developers should expect strict definitions (e.g., ~80% of median rents, program-dependent). 

• Don’t double-dip CMHC programs. MLI Select and the Affordable Housing Fund serve different aims; you can’t stack them. Plan your capital stack early.  

• Manufacturing & jobs matter. Prefab/tiny-home companies can access manufacturing, employment, export and environmental credits—separate from project grants—to reduce unit costs and scale production. 

• Eligibility is real. Funders review your team, 3 years of financials, and risk. Many good ideas need gap-analysis work (governance, revenue diversity) before submitting.  

• OREIO’s role: a growing hub (2nd Wednesdays) for investors to cross-pollinate and learn; yes, they’re recording sessions for members. 

What This Means for Canadian Investors: 
If you’re evaluating multi-family development, assume conventional financing alone may not pencil at today’s costs. Map your affordability commitments and non-dilutive funding sources early, then structure build-and-hold pro formas that satisfy program terms. Consider prefab partners to lock pricing, shorten timelines, and potentially qualify for manufacturing support on top of housing funds. 

Resources: 

• Grant Solutions Canada (intake): grantsolutionscanada.ca. Grant Solutions Cana 

• OREIO membership & events: oreio.org. oreio.org 

• Small Living Company (Ontario tiny homes; some through Home Depot): smallliving.co. smallliving.co 

🎧 Listen to the full episode here

---

Government Grants for Real Estate Developers, Q&A With Chelsey Fawcett 

1. What grants are available for Canadian real estate developers? 
   Available grants federal (e.g., CMHC/NHS), provincial, and municipal programs fund affordable rental supply; you can also stack tax credits, SHRED, employment, and manufacturing support where applicable. Canada Mortgage and Housing Corporation 

2. Do CMHC grants require affordable rents? 
   Yes—programs commonly require a portion of units priced below area median market rents for a set term, sometimes paired with forgivable-loan components. 

3. Can I combine CMHC MLI Select with the Affordable Housing Fund? 
   No; they’re separate programs with different aims, and double-dipping isn’t allowed. Build your capital stack around one or the other.  

4. What size of project makes sense to hire a grants firm? 
   Pipelines ≥ $1M (often 40–300+ units) benefit from strategy, lobbying, and underwriting support to increase award odds and speed.  

5. Are tiny homes eligible for grants? 
   Manufacturers can access manufacturing, employment, export, and environmental programs; project-based housing grants depend on the affordability criteria and use case. 

6. Why do housing grants favor build-and-hold? 
   Affordability goals require long-term rent commitments; build-and-hold ensures units remain below market for the program term.  

7. What documents do funders review? 
   Developers should be prepared to provide three years of financials, details on corporate structure, pro formas, and a risk analysis. Many teams will also need to complete a gap assessment before submitting.  

8. How do I make my project more “grantable”? 
   You should reserve affordable units, incorporate energy-efficient or low-carbon features, demonstrate diversified revenue streams, and engage potential funders before applying.

9. Is networking still valuable for funding? 
   Yes—groups like OREIO offer monthly education + cross-pollination with seasoned investors, service providers, and policy-savvy experts. 

10. Where can Canadian investors start? 
    Audit eligibility, choose the right CMHC/provincial/municipal lane, and speak with a grant strategist to stack non-dilutive capital. 

---

📜 Full Transcript

The full, cleaned transcript of my conversation with Chelsey Fawcett is available here for anyone who wants to dive deeper.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/unlocking-affordable-housing-in-canada-grants-prefab/id1100488294?i=1000735552999

On Spotify: https://open.spotify.com/episode/2J3dGKJZQ2WF3EuJZhM8IR?si=9tNmf-4yQxi53Dze4YdfGw

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/c8b16acf-d5f2-4131-997f-b1f81661654f/the-truth-about-real-estate-investing-for-canadians-unlocking-affordable-housing-in-canada-grants-prefab-homes-real-estate-investing-with-chelsey-fawcett

Audible: https://www.audible.ca/pd/B0G14XZNXB?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/88j90CtXBAI

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

• Do your investments match your long-term goals?
• Do you fully understand how your strategies work?
• Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

• Finding quality income properties
• Structuring the legal and tax side
• Managing the property manager and insurance provider
• Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Recorded: October 2025
Guest:️ Elizabeth Kelly, award-winning real estate investor, coach, and long-time educator 
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

In 2025, the phrase “buy a duplex, add a suite, and live off the cash flow” doesn’t hit the same.  The numbers literally don’t work when existing suited houses can be acquired for less $$. 

Canadian investors in Ontario, Quebec and BC (so the vast majority) are waking up to a new reality: the old formulas don’t work anymore. Rates are higher, values are soft, and “passive income” is harder to find north of the border. 

So what’s next? 

To unpack that, I sat down with Elizabeth Kelly — an award-winning real estate investor, coach, and long-time educator who’s been through multiple market cycles. Elizabeth built a 100+ unit portfolio, ran a full property management business in Northern Ontario, and today coaches investors on how to build real cash flow and resilience. 

Her message was clear: the future of investing looks less like “apartments” and more like “businesses.” 

The New Reality: Cash Flow Is Built, Not Bought 

Back in the early 2010s, Elizabeth and her husband could buy small-town multis with 5% down, get conventional financing, and cash flow from day one. 

Fast-forward to 2025: those days are gone. 

“You can’t copy a 2016 playbook and expect it to work in 2025,” she says. “Today, you have to build cash flow — not hope for it.” 

That means thinking like an operator, not just a landlord. The investors winning today are adding business income inside their properties — things like short-term rentals, storage, office rentals, or service-based tenants (salons, laundromats, co-working). 

Her own Northern Ontario building is a 33,000-square-foot former seniors’ home with multiple income lines: long-term rooms, offices, Airbnb units, and a salon. 
One property. Many businesses. Real cash flow. 

The Problem With “Government-Backed” Investing 

In the last few years, everyone and their cousin has been chasing CMHC MLI Select financing. Cheap debt, long amortizations — what’s not to love? 

Elizabeth’s warning: don’t build your business on government promises. 

“I don’t trust the government to keep giving cheap money forever. If policy changes, your whole model collapses.” 

She insists her portfolio must work without CMHC. The government may subsidize your project today — but the policy winds shift fast. If your deal only works with special financing, it’s not a deal. 

 From FOMO to Fundamentals 

Elizabeth spends much of her coaching time helping investors get out of trouble — overleveraged BRRRRs, private loans at 10–12%, or multifamily flips stuck mid-renovation. 

The root cause? FOMO and blind trust. 

“Too many investors handed off their judgment to brokers or mentors without understanding the math,” she says. “Education comes before execution.” 

She and her husband once spent $65,000 on mentorship and courses — and she says it saved them hundreds of thousands in mistakes. 

In 2025, education isn’t optional. It’s survival. 

The “Buy Box” That Fits You 

Every investor has a buy box — whether they know it or not. It’s your unique mix of: 

• Cash flow needs 

• Risk tolerance 

• Time commitment 

• Tenant type comfort 

• Capital available 

Elizabeth’s advice: stop copying someone else’s playbook. 
Your buy box should match your lifestyle — not your friend’s or your Instagram feed. 

If you’re too busy or risk-averse to self-manage tenants, consider passive, managed options like U.S. single-family rentals (SHARE) or private lending with conservative LTVs. 

If you’re hungry for higher returns, be ready to operate like a business owner — not a spectator. 

Partnerships and Private Lending: Trust, Verify, and Control 

After seeing partnerships implode, Elizabeth now only partners with people who bring capital, competence, and character. 

“My reputation is worth more than any one deal,” she says. 

For private lenders, she warns: if you’re not ready to take over the property, you’re not ready to lend. Always be on title, know your LTV, and underwrite the borrower’s plan yourself. 

And if you wouldn’t want to own that exact property in that exact neighbourhood? Don’t lend on it. 

 The End of “Passive” Canada? 

With high prices and thin margins, truly passive real estate investing in Canada is nearly extinct. 

That’s why more Canadians are exploring U.S. single-family rentals, where landlord laws are friendlier, PM fees are success-based, and you keep full title control. (That’s what we do at SHARE — simple, cash-flowing homes in stable markets.) 

Whether you go cross-border or stay local, the rule is the same: 
Control your income, don’t chase someone else’s yield. 

Life Balance, Cryo Therapy, and the Bigger Picture 

After all that talk about resilience, Elizabeth and I agreed on one more thing: take care of yourself. 

Her go-to recovery tool? CryoStrong in Markham and Scarborough — a two-minute, -120°F cold therapy chamber that boosts energy and reduces inflammation. 

Because at the end of the day, financial freedom means nothing if you’re too burned out to enjoy it. 

🎧 Listen to the full episode here

Final Thought 

Real estate is no longer a passive asset game. 
It’s a business — and your success depends on how well you can adapt, operate, and create value. 

“Build resilience and flexibility,” Elizabeth says. “Pivot faster than everyone else.” 

---

Rapid Fire: 10 Questions & Answers For Elizabeth Kelly 

1. What real estate strategies still work for Canadian cash flow in 2025? 
   Mixed-use, legal STRs, and commercial-adjacent plays that add a business to the building—so you can force income instead of waiting for appreciation.  

2. Should investors rely on CMHC/MLI Select for multifamily deals? 
   No—treat subsidies as bonus, not backbone; policy can change and derail financing timelines and exits.  

3. How can I define a real estate “buy box”? 
   Match property type, tenant profile, market, and activity level to your goals, risk tolerance, and time—your buy box, not someone else’s.  

4. Are partnerships safe for first-time investors? 
   Only if incentives, capital depth, and execution ability check out—and you can underwrite the deal yourself.  

5. Is private lending still worth it in Canada? 
   Yes, when you’re on title at sensible LTVs, with clear recourse and a takeover plan; bad operators and weak collateral are the real risk.  

6. What went wrong in New Brunswick for many investors? 
   Thin appreciation, higher non-owner property taxes, management challenges (even pests), and investor-driven price surges that weren’t sustainable.  

7. How do I “force” cash flow without a gut reno? 
   Add income lines: furnished mid-term rentals, STR suites where legal, small offices, storage, vending, or service tenants that fit zoning.  

8. What’s the fastest way to cut risk in a shaky portfolio? 
   Stabilize tenancy first, then refi/sell selectively; diversify income outside real estate to support debt coverage.  

9. Is passive income realistic for Canadian residential rentals right now? 
   Rare—most “passive” plays need either business income add-ons or different markets (e.g., U.S. SFRs with aligned incentives). 
   
10. What mindset do investors need in uncertain markets? 
    Resilience and flexibility: educate, pivot quickly, and balance optimism with brutal facts. 

---

📜 Full Transcript

The full, cleaned transcript of my conversation with Elizabeth is available here for anyone who wants to dive deeper into her journey as a real estate investor

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/apartments-vs-business-income-how-real-estate-investing/id1100488294?i=1000733146751

On Spotify: https://open.spotify.com/episode/2kn4yxTDairBBjX7Yw8xpe?si=Ag0sdiHlRRGsYKdLG4p6dg

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/37ec4987-4fe2-4e29-b93e-3928288c755f/the-truth-about-real-estate-investing-for-canadians-apartments-vs-business-income-how-real-estate-investing-is-evolving-in-2025

Audible: https://www.audible.ca/podcast/ITEM-NAME/B0FVPQ5Z6M?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/hoIwjG-PJrA

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

• Do your investments match your long-term goals?
• Do you fully understand how your strategies work?
• Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

• Finding quality income properties
• Structuring the legal and tax side
• Managing the property manager and insurance provider
• Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Recorded: September 2025
Guest: Luis Rivas
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

After 22 years in the federal government, Luis Rivas made a bold move—he retired early, cashed in his pension, and pivoted into real estate investing and coaching. In this episode, Luis shares how he went from speculating on Ottawa condos to building a multifamily portfolio across Canada and the U.S., and eventually becoming a head coach at WealthGenius. 

Luis opens up about the emotional toll of leaving a secure job, the lessons learned during COVID, and the mindset shift required to thrive as an investor. He breaks down his strategy for underwriting multifamily deals, targeting 5–6% cap rates, and why he’s now looking south of the border for better returns and landlord-friendly policies. 

We also dive into the challenges of being a landlord in Ontario, the importance of property management, and why Canadians must invest to secure their retirement. Luis shares his formula for calculating how big your portfolio needs to be to hit your lifestyle goals—and why legacy planning matters more than ever. 

📍 Catch Luis at the Expand Conference in Mississauga, October 31–November 2, where he’ll be speaking alongside top investors. 
🎤 I, Erwin Szeto, will also be speaking at the event. 
📲 Connect with Luis: Instagram & YouTube — @cashflow.rivas 

---

Real Estate Investing & Coaching with Luis Rivas: Top Questions

1. How did Luis Rivas transition from government work to real estate investing? 
   He retired early during COVID, cashed in his pension, and began coaching while building a multifamily portfolio. 

2. What was Luis Rivas’ first real estate investment? 
   Two pre-construction condos in Ottawa, which he later sold due to poor cash flow and lack of appreciation. 

3. Why does Luis prefer multifamily properties over condos? 
   Multifamily offers better cash flow, scalability, and commercial financing options, especially in secondary markets. 

4. What cap rate does Luis target in his investments? 
   He aims for 5–6% cap rates, with property management included in the underwriting. 

5. Why is Luis looking to invest in the U.S. market? 
   U.S. markets offer better cap rates, landlord-friendly laws, and more scalable property management systems. 

6. What advice does Luis give to new investors? 
   Get educated, join a community, and design your portfolio based on your lifestyle goals—not arbitrary door counts. 

7. How does Luis calculate the size of a portfolio needed for retirement? 
   He uses a formula based on monthly income goals, cash-on-cash return, and equity share to determine total portfolio value. 

8. What are the risks of investing in rural or tertiary markets? 
   Limited financing, property management, and appreciation can cripple deals if not properly managed. 

9. What is Luis’ take on Ontario’s rent control policies? 
   He believes they unfairly burden landlords and discourage investment, pushing many to look outside Ontario. 
10. What asset classes is Luis exploring next? 
    He’s researching self-storage and care homes, especially in Texas, for their automation potential and lack of rent control. 

---

🎧 Listen to the full episode here

📜 Full Transcript

The full, cleaned transcript of my conversation with Luis is available here for anyone who wants to dive deeper into his journey as a real estate investor

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/pensions-vs-real-estate-which-really-builds-wealth/id1100488294?i=1000729706240

On Spotify: https://open.spotify.com/episode/7FtMpPavD0xMB8riqiayGc?si=WFCkN9wDTu-GJo8sf8Jhxw&nd=1&dlsi=3d5328e1d2b54a60

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/41112347-107b-407a-ab97-b7a674773e7b/the-truth-about-real-estate-investing-for-canadians-pensions-vs-real-estate-which-really-builds-wealth

Audible: https://www.audible.ca/pd/B0FTMP1RMM?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/mWBef5KN5W4

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

• Do your investments match your long-term goals?
• Do you fully understand how your strategies work?
• Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

• Finding quality income properties
• Structuring the legal and tax side
• Managing the property manager and insurance provider
• Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Recorded: September 2025
Guest: Jimmy La and Kartik Singla, SDG Canada
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

---

Canada’s housing crisis isn’t going away—and developers like Jimmy La and Kartik Singla are stepping up with bold, scalable solutions. In this episode, I had an insightful conversation with the co-founders of SDG Canada about their ambitious infill development strategy, the benefits of CMHC’s MLI Select financing, and how their Clapperton Village project in Barrie is reshaping the rental landscape.

Key Takeaways

• SDG Canada is building modular, energy-efficient rental housing tailored for multi-generational families. 
• Their Clapperton Village development includes 100+ units across nine buildings, with plans to expand to 150. 
• The project is powered by CMHC’s MLI Select program, allowing 95% financing and long amortization terms. 
• Amenities include EV chargers, co-working spaces, gyms, and even air/water quality tracking. 
• The Missing Middle Conference on Sept 12 at the Fairmont Royal York will bring together mayors, ministers, and developers to tackle housing challenges head-on. 

Why It Matters:

With Ontario falling short of its housing targets and immigration numbers rising, the need for smart, scalable rental housing has never been greater. SDG’s approach—low-rise, family-friendly, and financially viable—is a blueprint for the future.

Don’t Miss These Two Game-Changing Events

Missing Middle Conference – September 12th, 2025 | Fairmont Royal York, Toronto

Canada’s housing crisis won’t be solved by chance—it requires bold ideas and collaboration. That’s exactly what the Missing Middle Conference is all about. Hosted by Jimmy La and Kartik Singla of SDG Canada, this one-day event brings together the brightest minds in housing and development, including:

• Mayor Olivia Chow (Toronto), the Mayor of Burlington, and other city leaders
• Federal and Provincial Housing Ministers’ teams
• Top developers, consultants, and investors
• And of course, Erwin Szeto, host of The Truth About Real Estate Investing for Canadians

If you care about the future of housing, want to understand how to profit from infill development, or are simply seeking to network with leaders driving change, this is where you need to be.

🎟️ Reserve your spot now at themmc.ca
💸 Use code MMC15% for 15% off tickets

Wealth Summit 2025 – September 27th, 2025 | Oakville & Online

After you’ve learned how to create millions through real estate development, it’s time to protect and multiply that wealth. That’s where the Wealth Summit 2025 comes in.

We’re bringing back the same energy and insight that made our Wealth Hacker Conferences legendary, where Grant Cardone and Jesse Itzler once took the stage, but this year, the focus is on what really matters for long-term financial freedom:

• Best practices in financial and estate planning
• How to build or replace a pension
• Protecting your wealth and minimizing taxes legally
• Wills, power of attorney, and intergenerational wealth transfer

This will be an intimate, high-impact event with only 40 in-person seats in Oakville, plus limited online access. If you’re serious about securing your financial future, you won’t want to miss it.

🎟️ Save your spot now
⚡ Don’t wait—seats are already filling up!

---

Smart Rental Development in Ontario: What You Need to Know

1. What is the Missing Middle in real estate?

The Missing Middle refers to housing types between single-family homes and high-rise condos—like duplexes, triplexes, and low-rise apartments.

2. Why is SDG Canada focused on infill development?

Infill allows them to add density in existing neighborhoods, using underutilized lots to build 6–60 unit rentals that meet real demand.

3. What is CMHC’s MLI Select program?

MLI Select is a financing program offering up to 95% loan coverage and long amortization for energy-efficient, affordable rental projects. 

4. How many units is SDG Canada currently developing?

They have 100 units in the pipeline across nine buildings, with plans to scale to 150 units in Barrie.

5. Why is Barrie a good market for rental development?

Lower land costs, supportive city planning, and proximity to new university campuses make Barrie ideal for scalable rental housing.

6. What kind of tenants are SDG’s buildings designed for?

Multi-generational families, professionals, and renters are seeking larger units with modern amenities. 

7. What amenities are included in Clapperton Village?

EV chargers, co-working spaces, gyms, saunas, air and water quality tracking, and shared outdoor areas.

8. Will MLI Select still be available in five years?

Yes—projects are grandfathered into the program with 50-year insured mortgages, making refinancing viable long-term.

9. How does modular construction help with sustainability?

It reduces waste, speeds up build time, and enables energy-efficient designs that exceed code by 45%.

10. What’s happening at the Missing Middle Conference?

Mayors, housing ministers, developers, and investors will gather to align on solutions for Canada’s housing crisis. 

---

🎧 Listen to the full episode here

📜 Full Transcript

The full, cleaned-up transcript from my conversation with the co-founders of SDG Canada is available here for anyone who wants to dive deeper into their infill development strategy, the role of CMHC’s MLI Select financing, and how Clapperton Village is reshaping the rental landscape in Barrie.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/canadas-housing-crisis-the-missing-middle-conference-2025/id1100488294?i=1000725725920

On Spotify: https://open.spotify.com/episode/7cOMIueDkR3utoSJ8J4UuH?si=IY8j3GTvSli8icVpgvWFvg

Amazon Music:https://music.amazon.ca/podcasts/930a-66d033586541/the-truth-about-real-estate-investing-for-canadians-canada%E2%80%99s-housing-crisis-the-missing-middle-conference-2025

Audible: https://www.audible.ca/podcast/ITEM-NAME/B0FQ4GN8T7?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/pGa85Erc9us

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

• Do your investments match your long-term goals?
• Do you fully understand how your strategies work?
• Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

• Finding quality income properties
• Structuring the legal and tax side
• Managing the property manager and insurance provider
• Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

Recorded: August 2025
Guest: Boubah, Co-Founder of the Small Ownership Landlords of Ontario (SOLO)
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

---

I’ll never forget our first non-paying tenant back in 2007.

The property was over 100 years old—charming in its own way—and brand new to us as owners. It was only our third investment property, and looking back… we really didn’t know what we were doing.

We missed obvious red flags, like the tenant’s SIN number being wrong. The two roommates were new to town, desperate for a place to rent, and we were too nice. We signed a lease. We accepted a personal cheque for the first and last month’s rent. And yes, we even handed over the keys before the cheque cleared. You know where this is going.

It was 2007, so expenses weren’t as brutal as they are today, but the ordeal still cost us around $10,000—including legal fees. The worst part? My partners were family. We were all upset, confused, and completely unprepared.

None of us even knew what an N4 was (a notice for eviction due to non-payment of rent). But our tenant sure did. When my family member handed him the notice at his workplace—Boston Pizza—he yelled at us to never come back.

Meanwhile, this same tenant was busy making himself at home—he even installed a heavy bag (the kind boxers use), drilled right into the living room ceiling. All while never paying a single dollar in rent. That was our introduction to Ontario’s rental system.

What no one told us in the early days was just how stacked the system is against landlords. How could I not change the locks on my own property when the tenant hadn’t even paid first and last month’s rent? Because if I did, the tenants could simply call the police—and in my experience, the police would side with them. The tenant. WTF?!

Fast Forward to Today…

It’s been nearly 20 years since that first painful lesson. Since then, I’ve coached more than 350 investor clients through their own journeys, and as a licensed Realtor since 2010, I’ve truly seen it all. And I can say with confidence: things have only gotten worse for landlords in Ontario.

That’s why I invited the co-founder of S.O.L.O. (Small Ontario Landlords Organization) onto my podcast. In this episode, we dive into the harsh realities of being a landlord in Ontario, where the system knows what’s broken, yet continues to side against landlords.

We talk about eviction parties, fraud teams, and how S.O.L.O. has grown into a 9,000-member grassroots movement. We also explore why so many Canadian investors are now looking south to landlord-friendly U.S. states—where the laws are clearer, the cash flow is stronger, and the risks are lower.

📅 Save the Date!

Cherry Chan and I are co-hosting an in-person meetup at our Oakville offices on Saturday morning, September 27th, 2025. Seating is extremely limited, so block off your calendar now. We’ll also be broadcasting the event as a webinar. And yes—lunch is sponsored, so you can stick around and network with fellow investors. Save a spot for yourself now

If you’re a landlord in Ontario—or thinking about becoming one—this episode is a must-listen. And if you’ve ever felt alone in the trenches, know this: you’re not. Tune in, learn, and let’s keep fighting the good fight… or, like me and so many frustrated landlords, consider taking the easier way out. 😊

---

🧠 10 Fast Facts Every Ontario Landlord Needs to Know

1. What is SOLO and who does it help?
SOLO (Small Ontario Landlords Organization) is a nonprofit that supports small landlords navigating Ontario’s rental system. It offers education, advocacy, and peer support to landlords facing tenant issues. 

2. Why is being a landlord in Ontario considered high risk?
Ontario landlords face long eviction timelines, limited legal recourse, and tenant-friendly laws that often delay resolution. The system is widely seen as stacked against property owners. 

3. How long does it take to evict a non-paying tenant in Ontario?
Evicting a non-paying tenant in Ontario can take 8 to 11 months, factoring in hearings, decisions, and sheriff scheduling. Professional tenants can stretch this process even longer. 

4. What is an N4 notice in Ontario real estate?
An N4 is a formal notice used by Ontario landlords to begin eviction proceedings for non-payment of rent. Many first-time landlords are unaware of this essential legal tool. 

5. Can landlords change the locks if rent isn’t paid in Ontario? 
No, Ontario law prohibits landlords from changing locks without a formal eviction order, even if rent hasn’t been paid. This legal restriction often surprises new landlords. 

6. What are eviction parties and why does SOLO organize them?
Eviction parties are community support events where volunteers help landlords clean up and emotionally recover after a tenant eviction. They reinforce that landlords are not alone. 

7. What is a professional tenant and why are they a problem? 
Professional tenants exploit Ontario’s rental laws to live rent-free for months by delaying hearings and abusing legal loopholes. They target small landlords who lack screening systems. 

8. Why are Ontario landlords investing in the U.S. instead? 
Many Ontario landlords are shifting to landlord-friendly U.S. states like Texas and Georgia for better cash flow, faster evictions, and stronger property rights. The risk-reward ratio is more favorable. 

9. What role does SOLO play in landlord advocacy?  
SOLO lobbies government officials, educates media, and supports legal reform to protect small landlords. It has met with the Premier and Minister of Housing multiple times. 

10. Is Ontario the worst jurisdiction for landlords in North America?
According to SOLO, Ontario is the only jurisdiction in North America where tenants can remain in a property without paying rent for extended periods. This makes it uniquely challenging for landlords. 

---

🎧 Listen to the full episode here

📜 Full Transcript

The full cleaned-up transcript from my conversation with Boubah is available here for anyone who wants to dive deeper into the nuances of protecting yourself as an Ontario landlord, navigating legal hurdles, and building a stress-free investment portfolio.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/ontario-landlord-crisis-tenant-fraud-evictions-solo/id1100488294?i=1000724039750

On Spotify: https://open.spotify.com/episode/1gkYYhLHSFDZZr6ddVsnxM?si=4GA2cXr2QNeoC21mpARscA

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/0186684c-5f4a-48ab-bc77-637c9138dfec/the-truth-about-real-estate-investing-for-canadians-ontario-landlord-crisis-tenant-fraud-evictions-solo-ca-solutions

Audible: https://www.audible.ca/pd/B0FP5NFL51?source_code=ASSGB149080119000H&share_location=pdp

Youtube: https://youtu.be/M_wHsRgi50Y

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

• Do your investments match your long-term goals?
• Do you fully understand how your strategies work?
• Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

• Finding quality income properties
• Structuring the legal and tax side
• Managing the property manager and insurance provider
• Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.

 

In 2003, a Canadian couple was eager to invest in real estate. They joined REIN, took the quick start weekend course, and learned the basics. But like many would-be investors, they stalled before buying their first property. The perceived barriers felt too high. Looking back, they admit that 2003 was an incredible buying opportunity — one they completely missed.

Not Understanding Hard, Scarce Assets and the Monetary System

By 2009, they finally took the plunge, buying a two-bedroom townhouse in Windsor. But their understanding of real estate was incomplete.
They knew about cash flow and mortgage paydown, but they didn’t grasp the third wealth driver: equity appreciation — especially how it’s tied to monetary policy and money printing.

After the 2008–2009 financial crisis, central banks responded with massive money creation. This was the starting gun for one of the greatest real estate bull runs in history. But at the time, they didn’t see it. Nervous about prices and the economy, they sold the townhouse for a small loss. Today, that same property would likely be worth four times as much.

The Comeback: Five Duplex Conversions in 15 Months

It wasn’t until 2017 that they committed fully. Inspired by re-reading Real Estate Investing in Canada while on vacation, they bought five single-family homes in Cobourg, Ontario, and converted them into duplexes — all in just 15 months.

The strategy worked. They targeted “awesome assets in awesome locations” — downtown, near the beach, and within walking distance to top schools. At the time, purchase prices of $420K plus $60–80K in renovations could be refinanced for $550K, enabling them to recycle capital quickly.

When the Math No Longer Works

Fast forward to today: those Cobourg properties are still owned, but high interest rates and today’s pricing have changed the picture. Two are cash-flow positive; four are not. With purchase prices now in the $750K–$850K range and renovations easily hitting $150K, new acquisitions simply don’t make sense.

The conclusion is blunt: If the spreadsheet doesn’t show positive cash flow after all costs, it’s not worth doing.

Pivoting to Lifestyle-Driven, Scarce Asset Investing

The answer wasn’t to quit real estate — it was to pivot.
The focus shifted to properties that are not only financially sound but also scarce and personally meaningful. That led to purchasing a luxury six-bedroom, ski-in/ski-out short-term rental in Mont-Tremblant.

Why Tremblant? Regulatory clarity, year-round demand, and true scarcity. There are only about 25 six-bedroom-plus STR properties on the mountain. The property commands up to $5,000 a night during peak season, and underwriting ensures it breaks even after all costs — property management, maintenance, and repairs — while serving as a vacation home.

The Next Step: Ground-Up Development

With the numbers no longer working for simple buy-and-hold rentals, the next logical move was into more complex, higher-return projects. The latest venture is a ground-up commercial development in Southwestern Ontario — a leap that combines market knowledge, a trusted partnership, and years of experience managing risk.

It’s part of a broader investment philosophy: as markets change, so must the investor. Where once a basic duplex conversion could deliver solid returns, today’s environment often requires greater complexity, higher risk, and more creativity to make the math work.

Looking Ahead: More Complexity, More Opportunity

The portfolio now spans:

1. Five duplex conversions in prime Cobourg locations
2. A luxury ski-in/ski-out short-term rental in Mont-Tremblant
3. A ground-up commercial development project underway

There’s also an eye on U.S. real estate for its landlord-friendly laws, better cash flow potential, and diversification benefits.

The core philosophy remains the same: own hard, scarce, uncorrelated assets — a private business, quality real estate in prime locations, and Bitcoin.

In a market where the easy wins are gone, this journey is a reminder that the math matters, scarcity wins, and adaptability is the real competitive edge.

Or… You Could Skip the Complexity Entirely

Not everyone wants to take on $2-million luxury ski rentals or ground-up development projects that require years of work, carry substantial risk, and often feel like another full-time job.

That’s why there’s SHARE — the alternative for Canadian investors who want:

• Positive cash flow from day one
• Low-interest financing
• Passive, done-for-you investing in landlord-friendly U.S. markets

With SHARE, you get the benefits of owning income property without the headaches of sourcing deals, managing renovations, or dealing with tenants. Your investment works for you from day one — simply, securely, and profitably.

Learn more and get started today at http://iwin.sharesfr.com

To Listen:

🦸‍♂️Household Hero? Here’s Your Next Step

If you’re a Canadian investor trying to build wealth safely and sustainably, Adam’s journey has valuable takeaways.

It might be time to revisit your current strategies—real estate, lending, or insurance—and ask:

• Do your investments match your long-term goals?

• Do you fully understand how your strategies work?

• Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

• Finding quality income properties
• Structuring the legal and tax side
• Managing the property manager and insurance provider
• Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.

---

Sponsored by… Me!

This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.

Interested in our systematic approach to real estate investing—the same one used by most of my podcast guests? Then check out:
📍 infinitywealth.ca/events

Till next time—just do it. I believe in you.

Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto

---

Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.