And that changes even for the same person over time. If you go back and look at my posts---going back a LONG time---I've been on Team Resale more or less forever.
So, what changed? Two things: the product and my circumstances.
The first is one that everyone knows. Up until 2019, points were points for all practical purposes. Sure, you couldn't use them on cruises, guided tours, etc. but those were poor uses of points anyway. I didn't qualify for the 10% Member discount at Olivia's, but I did qualify with a zero-fee Disney Visa, so who cares? Plus it would take a LOT of conch fritters to make up the difference. But now, points are differentiated, and that's especially true if (a) you want to an Epcot-ish home resort (b) for more than 15-ish years.
The second is more interesting. Both kids are out of the house and have started their own financial lives without a big pile of debt. At the same time, I am downsizing
and no longer need to live in the Really Expensive School District. So, money plays a different role in my life now. Finally, I've been staying in
DVC villas for years on timeshare exchanges, so long as I was willing to accept "the leftovers" after Members booked what they wanted.
After giving it some thought, I decided that if I was spending five figures on this anyway, I was going to do it in a way that did not require compromises, beause I no longer had to. And from a dollars-and-cents perspective, the thing I bought was about the dumbest possible choice. And I'm super happy about it, because I had the cash.
As a friend put it: "Thirfty 'til Fifty, then Spend to the End."
I'm not sure that is true. The average length of ownership of a resale contract is shorter than that, but that only measures the contracts that were resold, not the ones that weren't. I'll bet a mickeybar that more than half of the OKW contracts are still owned by the families that originally bought them. What's more, if someone's time horizon is ten years or less, I'd encourage them to consider renting rather than buying. Nothing is more flexible and lower risk than cash.