The kids are gone. The cottage covers the summers. Somewhere warm covers the winters. And the family home sits there, mostly or completely paid off, quietly worth more than anything else you own. Do you sell it and invest the proceeds — or keep it and turn it into a rental? Here’s what actually happens when you do the second thing, and why the tax consequences run deeper than the income line.
Mexico got the first country slot in this series for a simple reason: it’s close, the fideicomiso structure is well understood, and the Riviera Maya pipeline gave me a lot to work with in real time. Spain is the second country, and it’s a genuinely different conversation. No restricted zone. No trust structure. No fideicomiso fee sitting between you and the deed. You just… buy it. That simplicity is real, but it’s also where the easy part of this post ends, because Spain has spent the last eighteen months rewriting the rules around who gets to buy, what you can rent out, and how much of it the tax office takes on the way through.
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Every other post in this series has started with some version of “here’s why this country is worth your capital.” This one starts differently, because Italy real estate investing for Canadians has a problem the Mexico and Portugal posts didn’t have to deal with: right now, you may not be allowed to buy at all.
That’s not a typo and it’s not fearmongering to sell you a consultation. In January 2023, Canada introduced the Prohibition on the Purchase of Residential Property by Non-Canadians Act — the federal foreign buyer ban — and extended it in 2024 through January 1, 2027. Italy applies a reciprocity principle to non-EU buyers: if your home country lets Italians buy property there, Italy lets you buy property here. Canada’s ban broke that reciprocity, and Italy responded in kind. Americans and Brits sail through on long-standing treaties. Canadians, as of this writing, sit in a genuinely gray zone — some notaries will sign the deed, some won’t, and the honest answer to “can I buy in Italy” is “it depends which notary you ask.” I’m not going to bury that under a cheerful intro about olive groves. It’s the first thing you need to know, and it changes how this post is structured compared to the rest of the series.
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Mexico gets the phone calls. Portugal gets the long-term relationship.
Portugal real estate investing for Canadians is a fundamentally different proposition than the Mexico series I’ve been building out — and if I’m honest about my own shortlist, Portugal sits near the top of it, right alongside Mexico and Italy. Possibly ahead of both on one specific dimension: it’s the easiest of the three to actually execute. If you’ve read the Mexico introduction post, you know my bias toward proximity — a place you can reach for a long weekend gets used, and a place that requires nine hours in the air becomes a once-a-year commitment no matter how good the intentions were at purchase. Portugal breaks that rule and gets away with it. It’s not close. It’s not cheap relative to Mexico. And Canadians are still buying there in serious numbers, because Portugal isn’t selling proximity — it’s selling a legal system you recognize, a currency that isn’t going anywhere, EU market access, and a lifestyle case that Mexico, for all its yield, can’t quite match.
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This is the post where the series changes states — literally. Everything we’ve covered so far in Mexico has been Quintana Roo: the Riviera Maya guide, the Playa del Carmen real estate deep dive, and the Tulum post all operate under the same state regulator, the same RETUR-Q registration regime, the same Caribbean demand engine. Puerto Vallarta real estate runs on different rails. It’s in Jalisco, on the Pacific, with its own tax rates, its own regulatory trajectory, and — as of February 2026 — its own headline risk that we need to talk about like adults.
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In the Riviera Maya guide, I filed Tulum under “appreciation but submarket-dependent” and flagged La Veleta and Region 15 as oversupply risk before moving on. That’s a fair one-line summary, but it’s not a buying decision. Tulum is the most polarizing market in this series so far — it’s the one where the Instagram version and the spreadsheet version diverge the most — and it earns its own post.
If you haven’t read the earlier pieces, start with the Mexico introduction post for fideicomiso and T776 basics, then the Riviera Maya post for how Tulum stacks up against Playa del Carmen and Puerto Morelos. This post assumes you’re past that and specifically weighing a Tulum purchase.
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In the Riviera Maya guide, I called Playa del Carmen the yield-and-liquidity play of the region and moved on to Tulum and Puerto Morelos. A few of you pushed back on that — fairly. “Yield and liquidity” is a one-line verdict on a city of nearly 300,000 people with a dozen distinct submarkets, three tiers of buyer, and its own regulatory paper trail. This post is the deep dive Playa earns on its own.
If you’re new to this series, start with the Mexico introduction post for the fideicomiso and T776 basics, then the Riviera Maya post for how Playa stacks up against Tulum and Puerto Morelos. This post assumes you’ve already decided Playa is the city and want the neighbourhood-level, dollars-and-cents version.
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Mexico comes up constantly when Canadians start talking about buying abroad. It’s close, it’s cheap relative to home, the weather solves your February problem, and half the country seems to already have a cousin with a condo in Puerto Vallarta. But “close and cheap” isn’t a strategy — and Mexico has enough legal quirks, financing friction, and rental-market nuance that showing up with vibes and a vague sense that “Mexican real estate is a good deal” will get you into trouble.
This post is the primer. It won’t make you an expert on any single market — Riviera Maya, Puerto Vallarta, and Mérida each deserve their own deep dive, and those are coming. What it will do is give you the framework: where Canadians actually buy and why, how ownership legally works, how financing really functions (spoiler: not the way you’re used to), and the practical difference between running a short-term rental and a long-term one. By the end, you’ll know enough to ask the right questions instead of the obvious ones. Mexico is one of the locations I’m thinking of for a next investment.
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The cottage decision is behind me. If you followed along, you know how that analysis went — cottage vs. upsizing the primary residence, two mortgages vs. one, lifestyle purchase vs. an asset with optionality. The cottage won. And after one month of Airbnb hosting on Lake Huron, the numbers are pointing in the right direction — not cash-flow positive yet, not in shoulder season, but close enough that a full-season run (next year( should cover the carrying costs. That part of the thesis is holding.
So now what?
Continue readingIf you own a recreational property in Canada and you’ve been sitting on the fence about Airbnb, this is for you. Not the glossy version. The real one — with the actual dollar amounts, the mild anxiety of handing over your keys to strangers, and the moment your first guests left thoughtful items for the next family and a five-star review and you thought: okay, maybe this works.
One month in. Here’s what I know.
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