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.

 

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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. 

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📜 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 

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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.

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

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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.

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

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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.