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I bought into a thing that's kinda like timeshares, but it's through the company that runs most of the resorts. You get like 2 weeks a year for $300/week as long as you book within 45 days of the stay. Plus discounts on hotel rooms, flights, etc.
Basically it's where they rent rooms they're not likely to be able to on those days, so they're at least making some money.
So, if you like to travel in the off seasons, it works out really well.
It was only like $6k and $300 a year in maintenance fees.
A 10 year estimate of cost: That's 900/year + buy in and opportunity cost 1200/year. That's 2100/year for 14 days. So roughly 150-200/day locked in for a decade of short notice off season bookings. It's not bad, but it's also not good unless the rooms start going for 400+ in the future. Which even then you're only saving 2-3k/year for the restrictions, and if you don't use it fully the value quickly swings in their direction.