The Cottage Plan is Not About the Cottage

Every family thinks their cottage plan is going to be the exception. They won’t fight. They’ll share it equally. They’ll make decisions together. They trust each other.

Until someone wants to sell. Until someone can’t afford to maintain it. Until someone dies, and a new spouse or sibling-in-law wants access. Until one does all the work maintaining it. Until one of the kids starts treating it like their second home while the others can’t even get a week in July.

That’s when the plan stops being about the cottage. It becomes about fairness, control, resentment, and how people handle loss.

Lawyers can draft the structure. A trust, a co-ownership agreement, a holding company. But none of that holds up if the assumptions are wrong. And most families don’t realize what they’re assuming until it breaks.

They assume the kids want it. That they’ll cooperate and help out equally. That no one will ever need to cash out. That no one will remarry or go bankrupt or get sick.

That’s why I don’t start with documents. I start with dynamics.

Who’s likely to resent what? What happens when someone dies? Who really wants this, and who’s just going along?

Good planning doesn’t just preserve the cottage. It preserves the relationships. And that means making hard calls now—while you still can.

And when someone asks, "Is that tax efficient?" stop and ask a better question: "Is this family-efficient?"

Because the most tax-efficient plan in the world doesn’t mean a damn thing if your kids won’t speak to each other after you’re gone.

If you’re thinking about leaving the cottage to your kids, don’t ask, "What’s the best structure?" Ask, "What happens if this goes badly?" Then build something that can survive that.

If you’re ready for a plan that holds up in real life, book a call →

And if you’re not ready for documents but want help seeing the risks, I offer a separate clarity session before the legal work begins.

This site shares real-world insights from my work as an estate planning lawyer. It’s not legal advice, I'm not your lawyer, and it won’t cover every situation. But it will show you what tends to go wrong—and what usually holds up.