I hear this quite a bit, how “investors” are buying rental property investments in Toronto. There was a time when they would buy condos and call them investments, too.

That was a very bad idea. Long before the crash in Toronto condos, I discussed their pitfalls in podcasts and this newsletter. So, if you are tempted to buy a low-priced condo in Toronto right now, do what you think you need to do. However, I would never buy a condo in Toronto at any time and call it an investment.

In Toronto, with rental properties, many people bought properties with negative cash flow, thinking that prices would continue to rise and they would then sell for more than they were paying each month to cover the property's expenses. They were negatively cash-flowing at 2% mortgage rates, and now it’s even more of an adventure at 5%. Condos as investments and negative cash flow buildings are a dumb idea.

So, I turned to AskHank.ai and asked the question. Can you find me a Positive Cash Flow Rental in Toronto? The answer is below. In short, Hank did find a few, but regardless, I’d never buy any of them. I need a significant cash flow to be comfortable with the debt. I would also never buy a rental property in Ontario with the rules that favour tenants over landlords. Here is the analysis. Would you ever buy in Toronto? The good news is that we have taught AskHank.ai to hunt and analyze rentals in any city. Just ask the question, and if you don’t have the financial statements for the city's expenses, AskHank.ai will estimate. I use it to screen properties on a weekly basis.

While I appreciate the input from Ask Hank, I must disagree with myself. I’d never buy any of these.

Toronto Triplex Hank Analysis – Educational Estimates

Powered by Ask Hank™ — my cloned brain in an app

This information is for Educational Purposes only. Do not make portfolio changes without speaking with your financial advisor. I am not a financial advisor.

Summary Table

Property | Est. Price | Units | Rent/Unit | Est. NOI | DSCR | Cash-on-Cash | Verdict

8 Nineteenth St (Long Branch) | $1.20M | 3 | $2,800 | ~$62,000 | 1.02 | 1.5% | Hold

658 Dundas St W | $1.37M | 3 | $3,000 | ~$70,000 | 1.10 | 2.3% | Slight Value Buy

53 Alameda Ave | $1.30M | 3 | $2,800 | ~$65,000 | 1.05 | 1.8% | Hold

Hank 10 Rules + Bonus (Estimated Scoring)

· 1. The Hive Must Come First — Insider alignment & growth

· 2. Nature Knows Best — Simplicity & business durability

· 3. Recycle — Debt & capital discipline

· 4. Focus, Specialize, and Be Efficient — ROIC vs WACC, margins

· 5. Live in the Right Place — Competitive moats & geography

· 6. Little Things Over Time Become Big Things — Compounding

· 7. Be Strong, Fight Only When Needed — Prudent divestments

· 8. Probability of Success — Industry balance, resilience

· 9. Constant Feedback — Governance & adaptability

· 10. Listen to the Buzz — Market & analyst sentiment

Bonus: Delisting Risk — Market liquidity is low for all three, but acceptable.

Hank Score Summary

Property | Score | Verdict

8 Nineteenth St | 74 | Hold

658 Dundas St W | 84 | Slight Value Buy

53 Alameda Ave | 77 | Hold

Hank Commentary

8 Nineteenth St (Long Branch): A coastal hive — steady but higher maintenance. Long-term appreciation and easy tenanting but only modest cash flow.

658 Dundas St W: Central location, strong DSCR, and low taxes. Slight cash-on-cash positive makes it a Value Buy.

53 Alameda Ave: Stable returns and excellent future laneway potential; adding a fourth unit could boost DSCR above 1.25.

Key Metrics Summary

Metric | 8 Nineteenth St | 658 Dundas St W | 53 Alameda Ave

Cap Rate | ~5.2% | ~5.3% | ~5.0%

Equity Needed | ~$350k | ~$400k | ~$370k

Annual Debt Service | ~$63k | ~$73k | ~$68k

Est. NOI | ~$62k | ~$70k | ~$65k

Est. Cash Flow | ~$1k | ~$7k | ~$2k

Payback Years | 28 | 23 | 26

Closing Thought

According to Hank, “A triplex that breaks even in Toronto today is a future honey factory.” You’re not buying it for today’s nectar — you’re buying the comb structure: solid zoning, decent yield, and space to compound.

This information is for Educational Purposes only. Do not make portfolio changes without speaking with your financial advisor. I am not a financial advisor.

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