Tag Archives: Invesment

Canadian investor weighing second real estate options after buying a cottage — rental property, international real estate, and digital acquisition

Second Real Estate Investment: What Comes After the Cottage?

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?

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Cottage Airbnb — My Experience After 1 Month Hosting

If 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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