Why a 20-Year Canadian Finance Pro Drives 4.5 Hours to Buy $70,000 Cleveland Duplexes
By Erwin Szeto | Co-Founder, iWIN Wealth Planning
Recorded: May 2026
Host: Erwin Szeto, Truth About Financial Independence for Canadians
Guest: Carlos Rodriguez
Quick story before we get into this week’s guest.
Back at our September 2025 iWIN Wealth Summit, I walked through what I’ve been calling the 4-to-1 strategy. The idea is straightforward: $100,000 of investor capital combined with a $300,000 investment loan from the bank for a total of $400,000 deployed into professionally managed and index stock funds, including S&P 500 exposure.
Since that September presentation, the market has appreciated more than 13%. After management fees and borrowing costs at 5.2%, that translates into an estimated 40.6% return on the investor’s original $100,000. Leverage cuts both ways, of course, and suitability matters tremendously. But if you’re a real estate investor or someone pursuing FIRE, you already understand this principle intuitively. We’ve all used prudent leverage in real estate for decades.
Speaking of how leverage cuts both ways, Canadian real estate is in decline. Hamilton in particular is down 9% year-over-year, leading the entire country, as reported in the Globe and Mail. I’m glad I sold some Hamilton properties when I did. I wish I’d sold more.
Especially our Hamilton duplex. The tenant stopped paying rent. The LTB hearing got postponed, then postponed again. Seven months in, I’m $12,000 deep in lost rent, a couple thousand more in paralegal bills, and still waiting. Even with all the best screening practices, I couldn’t have foreseen the tenant’s health failing and his white-collar tech job laying him off in the same year. I’m holding the bag as a private social safety net at my own expense.
This is the world I’m operating in. And it’s the context that makes today’s guest worth your time.
Meet Carlos Rodrigues
Carlos Rodrigues spent 20 years in Canadian financial services. He holds licenses in mutual funds, life insurance both levels, and was a full mortgage broker, not just an agent, running four to five agents under him. He even started building out his own investment fund before the Canadian compliance costs shut that plan down.
So when somebody with that résumé tells me the math in Ontario doesn’t work anymore, I pay attention.
Today, Carlos is an active real estate investor focused on Cleveland, Ohio. He’s on the tools, on site, and driving four and a half hours each way from Hamilton to do it. He runs BRRRRs, joint ventures, and Section 8 rentals. He’s bought houses for as little as $70,000 that now appraise for over $170,000.
This isn’t a fantasy pitch. Carlos is honest about what active cross-border investing actually looks like.
The $70,000 Duplex Near the Cleveland Clinic
The headline deal in this episode is a 3,000-square-foot duplex Carlos bought for roughly $70,000, including a $24,000 wholesale fee. The property sits within a two-minute drive of the Cleveland Clinic, one of the largest hospitals in the United States, in a zip code that’s actively gentrifying.
The condition was rough. The main-floor toilet was on a diagonal and falling through the floor. But the bones were there. After renovations, the duplex appraised at $170,000.
This is the kind of math that doesn’t exist in the Golden Horseshoe anymore.
Section 8 Economics That Don’t Exist in Canada
One of the most eye-opening parts of the conversation was Carlos’s breakdown of how Section 8 (US government rental assistance) works for landlords.
He’s getting 20 to 30 percent above market rent through the program. He shared one tenant in the Coventry area, a retired nurse, who rents from him for around $1,400 per month. Of that, she pays $14. The federal voucher covers the rest.
“We’re considered the socialist country,” I said to him at one point, “but we don’t have anything like this in Canada.”
His strategy intentionally targets Section 8 because it builds a strong rent base. If the broader economy turns down and tenants in other rental classes start losing jobs, his voucher-backed rent keeps flowing.
There’s risk on this side too. Federal funding can change. But compared to my Hamilton duplex, where a job loss meant seven months of zero income and a paralegal bill, the contrast is hard to ignore.
What the US Lending Market Is Doing Right Now
Carlos shared an email he just received from a US broker offering 100% loan-to-cost financing. That’s 100% of the purchase price plus the full renovation budget, lent against the after-repair value.
This is the kind of headline that triggers 2008 comparisons. Both of us went out of our way to address that. As Carlos put it, in 2008 lenders were putting a mirror in front of borrowers’ faces and lending if it fogged. That isn’t what’s happening now. These loans go through proper appraisals, lead-safe certifications, rental licensing inspections, and the rest of the US regulatory apparatus. But the credit is loose, and that’s worth knowing.
For context, just a few weeks before that email, brokers were quoting Carlos 90% loan-to-cost. The market is moving.
The Joint Venture Partner Who Panicked
Carlos didn’t sugar-coat the operator headaches. His most painful recent story involved a joint venture partner who, between Carlos leaving the site for a Home Depot run and returning, expanded the renovation scope from $65,000 to over $100,000.
“The unfortunate thing with joint venture partners,” Carlos said, “is when people start to get uncomfortable, they start trying to shift to alleviate that pain. And sometimes they do things that, well, over-renovate.”
It’s a useful warning for anyone considering JV deals across a border, especially when one partner has Ontario-market mental models and the other partner is dealing with Cleveland-market realities. The numbers in Cleveland support a different finish level, different price points, and different exit timelines. Mismatched expectations cost real money.
The Contractor Problem
Cleveland is busy. Contractors are scarce. Carlos’s contractor ghosted him a week before closing on his current project.
He also raised a less-discussed reality: the immigration crackdown in the US is hitting the construction labor pool. Many of the most reliable workers in his market are of South American descent, and ICE enforcement has made them cautious about advertising their services publicly. Phone numbers are gone. Contractors now communicate through Instagram DMs and voice-over-IP. Even legal workers are wary.
That tightens the supply of skilled trades. If you’re going into Cleveland for active renovation work, this is a real cost you need to budget around.
Cleveland Appreciation: Real Numbers
Carlos was disciplined about underwriting. His own deals assume 1.5 to 2 percent annual appreciation. He expects 2 to 4 percent over the next five years.
Recent actual appreciation in Cleveland: 7 percent year over year.
The gap between what he underwrites and what he’s actually getting is what builds margin of safety into his deals. This is the same lesson Sarah Coupland made last week, working backward from conservative resale values rather than chasing the optimistic case.
The Side Yard Program
One small detail that stuck with me: Cleveland has a side yard program where if your principal residence sits next to a vacant lot owned by the land bank, you can buy that lot for $100. If your investment property sits next to it, you can buy the lot for $500.
Compare that to the Golden Horseshoe, where lots run hundreds of thousands of dollars. These are different markets with different math. The strategy you use in one doesn’t transfer to the other.
The Bottom Line
Canadian real estate isn’t dead. But the conditions that made it a passive vehicle for the average investor aren’t like they used to be. If you want to be an active operator, treat real estate as a business, and drive four and a half hours each way to do it, the Carlos Rodrigues path is open to you.
If you want passive, you need to look elsewhere. Landlord-friendly US markets through the right partners. Leveraged stock-market positions through investment loans. Small-business acquisition. These are the paths the show will keep covering.
Diversify. Pacify. Get your time and your peace of mind back.
That’s the next chapter.
Want the Whole Investment Loan Strategy Walked Through Live?
This Saturday, May 30, 2026, I’m hosting a free training on the strategy that produced the 40.6% return I mentioned at the top of this post. It’s hybrid: in-person at the iWIN office in Oakville, or join on Zoom from anywhere. Hard start at 9:00am Eastern, hard stop at 10:30am.
In those 90 minutes, I’m walking through:
- The complete $100,000 investment loan structure
- The math, what $433 a month actually buys you over 5 and 10 years
- Every loss scenario, what happens when the market drops 20%, 30%, 40%
- How this fits alongside, not replacing, a real estate portfolio
- Live Q&A, bring questions, bring skepticism
In-person seats are capped at 40 and they always go. If you want to be in the room, register today.
Saturday May 30, Hybrid (Oakville + Zoom): infinitywealth.ca/20260530
Tuesday June 2, Zoom only at 8pm Eastern: infinitywealth.ca/20260602
Both events cover the same content. Pick whichever fits your schedule.
To Listen:
Apple: https://podcasts.apple.com/ca/podcast/20-years-in-canadian-finance-now-he-only-buys-%2470k/id1100488294?i=1000770024019
You’ve Built Wealth. Now It’s Time to Understand It.
You’ve Built Wealth. Now It’s Time to Understand It.
After dozens of consultations, I’ve noticed the same pattern again and again: most investors have built real wealth, but they’re not confident they can retire from it. They’re sitting on $2M–$5M in property but feel cash-flow poor. They’re paying more tax than they should because everything is held in personal names. They have no liquidity, no insurance strategy, and no clear plan for what happens if something happens to them. And almost every single client tells me the same thing: “I don’t actually know what retirement looks like for us.”
Real estate builds equity, but it doesn’t automatically build freedom. Without a coordinated plan for taxes, income, protection, and exit strategy, investors often end up working harder in retirement than they did in their 30s. That’s why I created the Wealth Freedom Blueprint – a simple, practical guide to help you understand where you stand today, what gaps are costing you money, and how to turn the wealth you’ve built into a life you can actually live.
Download your free Wealth Freedom Blueprint
Disclaimer:
As a committed advocate for transparent and responsible investing, I disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer. I am also a licensed insurance agent with Open Concept Financial Group. The investment loan strategies discussed are for educational purposes only and are not a guarantee of approval or performance. Past performance is not indicative of future results. Every investor should do their own due diligence.
Final Thoughts
Whether you’re building wealth, protecting it, or preparing to transition it, you deserve a clear, tax-smart strategy that works in real life.
That’s what iWIN Wealth Planning is here for.
This is how we’re creating predictable, stress-free wealth for Canadian families…
so you can enjoy the life you’re building.
Book your Wealth Planning Call
Sponsored by… Me!
This episode isn’t sponsored—except by my wife Cherry and me. Real estate investing is our life. It’s helped us build wealth and achieve peace of mind about retirement and our children’s future.
Till next time—just do it. I believe in you.
Erwin Szeto
W: erwinszeto.com
FB: facebook.com/erwin.szeto
IG: @erwinszeto
Disclaimer
As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.
My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.
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