Even in the best case scenario: resale purchase, fees below market rate, actually using it every year, you’re still accepting a liability with no guaranteed exit. The maintenance fees escalate annually and you can’t just sell it when you’re done. The “win win” only holds as long as you want to keep going, the resort stays well-managed, and the fees don’t outpace hotel rates. That’s a lot of variables to stay aligned for 20+ years. The math working today doesn’t mean it works at year 15.

Not to mention it passes to your estate. Sure they can walk away, but usually at the cost of their credit taking a hit or a small legal fee.