The Canadian Real Estate Investor

If you bought a Canadian condo near the peak of the market, you may now be underwater, or losing money every month just to keep it. In this episode, Daniel and Nick tackle one of the hardest decisions facing Canadian homeowners and real estate investors: should you hold on, rent the property out, or sell at a loss? They examine real examples from the GTA, pre-construction deals, power-of-sale transactions and struggling flips before laying out a practical framework for making the decision without letting fear, ego or sunk costs take over.
You’ll learn:• The difference between a forced seller and a scared seller• Why your monthly “bleed rate” matters more than the paper loss• How to calculate the true cost of continuing to hold• Alternatives to selling, including refinancing, renting and adding units• The legal risks of walking away from a pre-construction purchase• Why Canadian mortgages generally don’t allow you to simply walk away• How taxes and capital losses may affect the decision• Warning signs that negative cash flow is damaging your personal finances• The one question every underwater investor should ask: “Would I buy this property today?”Selling at a loss doesn’t automatically mean you failed. Sometimes protecting your credit, liquidity and ability to invest again is the smartest move you can make.
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Nick & Dan are joined by Jacob Cohen, President of Daniels Corp. for a field report from inside a GTA development company. Why an activity slowdown worries developers more than falling prices, which input broke first: land, construction costs, rates, or sales velocity, and what still makes sense to build when almost nothing pencils.
With starts near zero since 2023, the completions that should land in 2027–2029 aren't coming. Jake walks through the math, the industry's sudden rush into purpose-built rental after 30 years of ignoring it, whether the investor-driven condo model is paused or finished, and what he'd tell an investor weighing pre-construction today.
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Brandon Sage of Landlord Property Management joins us to discuss everything you need to know about owning and managing property and tenants.
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Real estate searches in Canada just hit a five-year high, and Nick and Dan answer the nine questions Canadians are Googling most. Fixed vs. variable in 2026, what to do if you can't afford your renewal, where prices are headed, the best cash-flow cities, whether to incorporate your rentals, the new Airbnb rules by province, and how to save six figures on the principal residence exemption. Plus two rapid-fire bonuses: rent vs. buy, and the new 30-year amortization. No filler... just the answers.
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Multiplex starts just passed tower starts in Toronto for the first time. Condos have stalled, and the big builders aren't structured to build on tight low-rise sites, while most GCs can't properly analyze them. That gap is the whole opportunity.
We are joined by the founders of Reside Properties Ryan & Mattison, a Toronto developer with an unusual stack: years as a general contractor, time as MPAC counsel working with planners on highest-and-best-use, and a legal background in development. They build it, they know how the city values the land, and they know where the traps are. Zero vacancy across the portfolio.
We get into the product thesis; custom-home-quality condo alternatives with dedicated entrances, separate utilities, and real millwork, and why that holds up when the market turns. Then we spend the bulk of the episode on the five ways these deals blow up:
The contractor who wins on price and makes it back in extras
Timeline slippage: financing, utility connections, trades, inspections
Fantasy rents that kill your refinance
Building the wrong units for the micro-market
One zoning misstep that turns $30K in DCs into $200K
Plus how Reside partners with landowners, and why the hard part has permanently shifted from approvals to execution.
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