How Canadians Can Win in U.S. Real Estate in 2026 (Without Betting on Appreciation)
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.
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:
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.
Leave a Reply
Want to join the discussion?Feel free to contribute!