From False Start to 5 Duplexes, a Ski Chalet, and Ground-Up Development: How Increasing Complexity Drives Returns Today

 

In 2003, a Canadian couple was eager to invest in real estate. They joined REIN, took the quick start weekend course, and learned the basics. But like many would-be investors, they stalled before buying their first property. The perceived barriers felt too high. Looking back, they admit that 2003 was an incredible buying opportunity — one they completely missed.

Not Understanding Hard, Scarce Assets and the Monetary System

By 2009, they finally took the plunge, buying a two-bedroom townhouse in Windsor. But their understanding of real estate was incomplete.
They knew about cash flow and mortgage paydown, but they didn’t grasp the third wealth driver: equity appreciation — especially how it’s tied to monetary policy and money printing.

After the 2008–2009 financial crisis, central banks responded with massive money creation. This was the starting gun for one of the greatest real estate bull runs in history. But at the time, they didn’t see it. Nervous about prices and the economy, they sold the townhouse for a small loss. Today, that same property would likely be worth four times as much.

The Comeback: Five Duplex Conversions in 15 Months

It wasn’t until 2017 that they committed fully. Inspired by re-reading Real Estate Investing in Canada while on vacation, they bought five single-family homes in Cobourg, Ontario, and converted them into duplexes — all in just 15 months.

The strategy worked. They targeted “awesome assets in awesome locations” — downtown, near the beach, and within walking distance to top schools. At the time, purchase prices of $420K plus $60–80K in renovations could be refinanced for $550K, enabling them to recycle capital quickly.

When the Math No Longer Works

Fast forward to today: those Cobourg properties are still owned, but high interest rates and today’s pricing have changed the picture. Two are cash-flow positive; four are not. With purchase prices now in the $750K–$850K range and renovations easily hitting $150K, new acquisitions simply don’t make sense.

The conclusion is blunt: If the spreadsheet doesn’t show positive cash flow after all costs, it’s not worth doing.

Pivoting to Lifestyle-Driven, Scarce Asset Investing

The answer wasn’t to quit real estate — it was to pivot.
The focus shifted to properties that are not only financially sound but also scarce and personally meaningful. That led to purchasing a luxury six-bedroom, ski-in/ski-out short-term rental in Mont-Tremblant.

Why Tremblant? Regulatory clarity, year-round demand, and true scarcity. There are only about 25 six-bedroom-plus STR properties on the mountain. The property commands up to $5,000 a night during peak season, and underwriting ensures it breaks even after all costs — property management, maintenance, and repairs — while serving as a vacation home.

The Next Step: Ground-Up Development

With the numbers no longer working for simple buy-and-hold rentals, the next logical move was into more complex, higher-return projects. The latest venture is a ground-up commercial development in Southwestern Ontario — a leap that combines market knowledge, a trusted partnership, and years of experience managing risk.

It’s part of a broader investment philosophy: as markets change, so must the investor. Where once a basic duplex conversion could deliver solid returns, today’s environment often requires greater complexity, higher risk, and more creativity to make the math work.

Looking Ahead: More Complexity, More Opportunity

The portfolio now spans:

1. Five duplex conversions in prime Cobourg locations
2. A luxury ski-in/ski-out short-term rental in Mont-Tremblant
3. A ground-up commercial development project underway

There’s also an eye on U.S. real estate for its landlord-friendly laws, better cash flow potential, and diversification benefits.

The core philosophy remains the same: own hard, scarce, uncorrelated assets — a private business, quality real estate in prime locations, and Bitcoin.

In a market where the easy wins are gone, this journey is a reminder that the math matters, scarcity wins, and adaptability is the real competitive edge.

Or… You Could Skip the Complexity Entirely

Not everyone wants to take on $2-million luxury ski rentals or ground-up development projects that require years of work, carry substantial risk, and often feel like another full-time job.

That’s why there’s SHARE — the alternative for Canadian investors who want:

• Positive cash flow from day one
• Low-interest financing
• Passive, done-for-you investing in landlord-friendly U.S. markets

With SHARE, you get the benefits of owning income property without the headaches of sourcing deals, managing renovations, or dealing with tenants. Your investment works for you from day one — simply, securely, and profitably.

Learn more and get started today at http://iwin.sharesfr.com

To Listen:

🦸‍♂️Household Hero? Here’s Your Next Step

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

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

• Do your investments match your long-term goals?

• Do you fully understand how your strategies work?

• Would a more conservative approach offer better peace of mind?

Real estate remains a powerful tool for building wealth, especially with careful underwriting and due diligence. Insurance can be useful too—but only if it supports your broader financial goals.

Need help with conservative, peace-of-mind investing—backed by Wall Street-style due diligence—plus financial planning with your best interests at heart? 

📅 Book a call

Until next time, happy Canadian and USA Real Estate Investing.

Erwin Szeto,

Your Cross Border Investment Guy

Why I’m Investing in the U.S.

I’ve been investing in Ontario since 2005. It’s been a great run—starting with properties in the $100Ks, now reaching $800K–$1M. How much higher can it go? I don’t know.

The remaining appreciation potential doesn’t justify the risk. That’s why I advise clients to look to the U.S., where rental properties range from $150K–$350K USD, with rents between $1,400–$2,600/month.

These cash-flowing numbers are night and day compared to Canada. Plus, landlords have rights, there’s no rent control, and income is in U.S. dollars—which are stronger than Canadian dollars.

If you don’t believe that U.S. dollars are stronger, ask 100 non-Canadians what they’d prefer to be paid in.

To regain control of your retirement, check out the cash-flow properties at:
👉 iwin.sharesfr.com

How SHARE Makes It Easier

The best part? My U.S. investments are more passive than my Canadian ones. I work with SHARE, an asset manager that guides me through the entire process.

SHARE helps with:

• Finding quality income properties
• Structuring the legal and tax side
• Managing the property manager and insurance provider
• Saving time and money with preferred rates

They even advise on when to refinance or sell. SHARE supports investors across the U.S., which is why I plan to own in Tennessee, Georgia, and Texas. It’s like having a JV partner—without giving up ownership or control.

Final Thoughts

If increasing cash flow is your goal, I don’t know of a better strategy for most Canadians. Once more: iwin.sharesfr.com is where to see what boring, cash-flowing investing looks like on the path to financial peace.

This is how I’m making real estate investing great again—for my family and hopefully for yours too.

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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.