This is an interesting question and I am an interesting case study. As you can see from my username I set up my account to learn more about
DVC in 2013. We bought our first contract, VWL, for about $60 per point in 2013. Then we bought a BLT contract for $115 in 2014. We sold both of our contracts in 2018 due to a kitchen remodel that went way over budget (as if any home remodel ever comes in anywhere near budget). We sold the VWL for about $80 and the BLT for about $120.
We are now at a point where we have cash and could buy back in. However prices are much higher now and we have decided the value just isn't there anymore. So, in a way, you could say I "regret" buying DVC because given the choice right now I'm not buying. And if I hadn't sold in 2018 I'd probably be selling now. Here's why:
1) Our kids were born in 2009 and 2012. During the stroller/nap years a villa close to the park is a huge plus. The ability to stay at a Crescent Lake resort and walk to two parks is an amazing benefit when you're pushing a double stroller. Seriously, buses are a much, much worse experience when you have a double stroller.
2) When your kids are like 4 years old it's easy to know you're going to go to WDW every year for at least the next several years. But now that they are 10/12 do they want to go to WDW every year for the next 5-10 years? I don't know about that. Do college age adults really want to go to WDW with their parents when they are home from school? I don't think I would have wanted to do that. So there just doesn't seem to be enough time left for WDW vacations to make the DVC purchase worth it.
3) Renting points. We went in 2021 and stayed at BWV and I rented points from David's Vacation Rentals for I think $18 per point. Maybe it was $20, but the idea is that renting is a viable option. With the dues about $10 that means the points only cost you $10 net to rent. With $140 prices that's like 14 years for a break even range (these are all rough numbers, but you get the point). So if it's going to take 14 years to break even but my kids may only want to go the next 5 years.... you see where I'm going with this.
4) Staying off site. There are a ton of offsite options. Now, offsite kinda sucks I admit. But it sucks a lot less when you have teens than when you have toddlers (see point #1). And it's like WAY cheaper to stay offsite. I did a quick look and there's a suites place at Disney Springs where you can get a 1 BR villa (which is what we got with DVC) for like $400 per night. DVC just doesn't make financial sense at $140 per point when you have these other alternatives. A 1BR villa at even OKW (which I think is the cheapest) is like 220 points for a summer week, at $20 per point renting that's $4,400, about $600 per night. So it's almost double what it would cost to stay at a Disney Springs place. Again, these are rough numbers but you get the idea.
5) changes at WDW. I'm not opening this Pandora's box too much. But the idea is a Disney vacation has changed quite a bit in the 10 years since we originally bought. Back when we bought they still had paper fast passes, or maybe they were right at the transition to FP+, but now FP+ doesn't even exist. A DVC purchase is a long term commitment, like getting a dog, and it's difficult to know what to expect from a Disney trip 10 years from now. By choosing to rent points or stay off site I keep flexibility and that has value.