I own a timeshare (Wyndham), and I love it. But, I specifically picked a location that I would use, that didn't cost a lot of points for value, that was highly flexible (love the point system, and not the "you're stuck with this week, location, and timeframe" system), that had very low maintenance fees (and yet wasn't old and falling apart), and that allowed point pooling (so I could skip a year). Right now, I get the equivalent trade of a 2 bedroom in "high season" for a week per year for $818.76 all in at my chosen site (Williamsburg). Usually, I throw in $39 every 3 years to "pool" my points and get 2 weeks in Orlando (or 2 5-6 vacations I like) for 2 years in a row (so 28 days every 3 years), since my timeshare does go farther in value season in Orlando.
Now, the points don't go as far in a city location (like NYC), although I am considering 4 nights in a 2 bedroom in dowtown NYC for next year with pooled points for 2 years worth of points, so that would be $1675ish cost equivalent out of my pocket all-in for that type of vacation. But then again, looking at high season hotel rates for 2 separate rooms or a single 2 bedroom suite in NYC for that timeframe, and I can't find anything really under $900/night + taxes (best for NYC seems to be $450/night x 2 rooms for summer rates), so if I use it the timeshare that way, I'm still coming out way ahead.
As of now, I've had it for 15 years, so everything is bonus (and has been since the year we bought). We did buy direct, and I would encourage a small direct contract with resale points for what you want, so you get the bennies of direct with the low cost of resale. When we bought, we spent $10K...I assumed that would be my vacation fund, and never an investment. I mean, if I get anything ever back out of it, I'd be shocked. But I plan on continuing to use it for pretty much the next 40-50 years (especially having the ability to winter in Florida near family in retirement

, so I have no plans to punt it anytime soon.
I mean, I didn't buy DVC b/c I didn't want the 50 year limit...when I bought, 50 years would have only got me to my mid-70s...and I totally plan on warm weather for winter longer than that

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