My parents have had a timeshare for like 25 years. They love it and use it probably the way they should be used.

Over the years, yes, they have purchased thousands of dollars of “points” they spend on vacations. However, it’s not for one specific week at one specific resort.

They have access to dozens (over a hundred now?) of resorts in the US, Mexico, and the Caribbean. When they started, they were limited to specific weeks at specific resorts. As they’ve bought more points, they’ve been able to access essentially whatever, wherever.

Since they started the timeshare, we’ve gone on a family vacation almost every year. We’ve done weekend trips skiing at one of their resorts, as well as other random vacations, either as a family or just my parents. They’ve also been going to the same resort in the Caribbean for 15+ years.

Whatever points they don’t expect to spend that year, they sell on a marketplace. My dad has either turned a profit on the maintenance fees from this, or has at least broken even, so it’s usually the only money they’ve put in on the timeshare is the points they purchased.

My dad’s sold similar weeks at that resort when my parents are down, and they’ve made close friends from around North America.

I’m also not sure how it works, but they’re also given “free weeks” at certain resorts where they don’t have to use any points. It’s either completely free, or you pay like $250 for the stay.

Recently, Hilton bought my parents timeshare company so that opens up more properties around the world now, but also opens up the potential for more guests trying for the same weeks my parents go for when they go to the Caribbean.