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: January 2026

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

Guest: Serena Holmes, Award-winning Marketing and Business Professional, Podcaster and Author

Folks, welcome back to the show. 

If you’ve been listening to me for a while, you know I am obsessed with control. I like to own the title. I like to control the bank account. I like to know that if everything hits the fan, I can drive to the property and change the locks. 

Today’s guest, Serena Holmes, is here to share a cautionary tale that proves exactly why control is everything. 

Serena is a powerhouse. She built and exited a multi-award-winning marketing agency, she’s a Realtor, an author, and the host of the Inspired to Invest podcast. But a few years ago, she did what many busy entrepreneurs do: she tried to move from “active” income to “passive” investments. 

She invested in syndicated mortgages. She did private lending. She diversified into 18 different income streams. 

And then? They all went to zero. 

We’re talking about the collapse of major operators (like the Windrose Group) where hundreds of investors lost millions. Serena is open, vulnerable, and incredibly smart about what went wrong and, more importantly, how she is rebuilding. 

If you are thinking about handing your money over to a “hands-off” operator, or if you are raising capital yourself and want to do it without ending up in court, you need to read this. 

🎧 Listen to the full episode here

10 Capital Raising & Risk Questions Answered in This Episode 

1. What happens when “Passive” Investing goes wrong? 

Serena shares the reality of investing in syndicated mortgages and unsecured promissory notes. She thought she was diversified with 18 streams of income, but when the operators failed (due to fraud, mismanagement, or market shifts), every single stream dried up. The lesson: Diversification doesn’t help if the underlying asset structure is flawed. 

2. What does “If you’re not first, you’re last” mean in lending? 

This is the golden rule of private lending. Serena explains that if you are not in the first mortgage position, you are likely in trouble when a deal goes south. Unsecured notes or second/third positions often get wiped out completely during a power of sale or bankruptcy. 

3. Can you trust a “Guaranteed” return? 

No. We discuss how operators who scaled too fast (buying 600+ homes in 6 years) couldn’t refinance quickly enough when rates spiked. If an operator promises high returns without explaining the risks or having the liquidity to back it up, run the other way. 

4. Why is “Control” the most important word in investing? 

Serena admits she “shot herself in the foot” by giving away control. When you own the property on title, you have options. When you are a passive investor in a limited partnership or a promissory note holder, you are at the mercy of the operator’s competence and ethics. 

5. What is the reality of the GTA Listing Market right now? 

Serena is an active Realtor in the Durham/Toronto area. She notes that sellers are still stuck in 2022 pricing. She has listings where sellers turn down offers, only to receive lower offers months later as the market continues to soften. The “hold and hope” strategy is hurting sellers right now. 

6. Is it worth suing to get your money back? 

Serena has spent between $40,000 and $50,000 in legal fees trying to recover funds, with little to show for it yet. She highlights the harsh reality of the Canadian legal system: it is expensive, slow, and often, the money is simply gone. 

7. Why are Canadian investors moving capital to the USA? 

We discuss the “capital flight” to the US. Serena notes that the US GDP is expected to grow twice as fast as Canada’s . Between landlord-friendly laws, the 1031 exchange (tax-deferred selling), and better cash flow, many of her clients are pivoting south . 

8. What is the “Wild West” of Capital Raising? 

There was a time (and still is) where people raised millions on Facebook with zero compliance. Serena now works with M1 Real Capital, coaching investors on how to raise capital legally, ethically, and responsibly. You can’t just take money from people without the right paperwork and disclosure. 

9. How do you spot a “Con Artist”? 

I shared a quote from the book The Confidence Game: “Con artist” is short for “Confidence Artist.” Serena shares a story about seeing a prominent operator who looked the part—tall, commanding presence, confident on stage—who eventually went bankrupt owing investors millions. Confidence does not equal competence. 

10. What is the best way to rebuild after a loss? 

Serena’s advice is to get back to basics. She is focusing on her active income, helping others avoid her mistakes through coaching, and planning to return to purchasing multifamily properties where she controls the asset and the operations . 

🎧 Listen to the full episode here

My Final Thoughts 

Folks, I have seen too many people lose their life savings because they chased a high interest rate on a piece of paper. 

Real estate is a fantastic asset class, but it is not magic. It requires due diligence. If you don’t understand where the yield is coming from, or if you don’t have your name on the title, you are taking a massive risk. 

Serena’s story is a powerful reminder that return of capital is far more important than return on capital. 

If you want to connect with Serena to learn about compliant capital raising or just to follow her journey, you can find her on Instagram at @serenaholmesofficial or listen to her podcast, Inspired to Invest . 

As always, thanks for listening (all 17 of you!), and keep hustling. 

---

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/from-18-income-streams-to-zero-a-real-conversation/id1100488294?i=1000748566542

On Spotify: https://creators.spotify.com/pod/profile/erwinszeto/episodes/From-18-Income-Streams-to-Zero-A-Real-Conversation-About-Risk-in-Real-Estate-e3eo0bg 

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/e33922c4-8771-4520-b047-ec9d8c27b40b/the-truth-about-real-estate-investing-for-canadians-from-18-income-streams-to-zero-a-real-conversation-about-risk-in-real-estate

Audible: https://www.audible.ca/podcast/ITEM-NAME/B0GKXS1MCP?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/5t4Ht_vwq4o

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.