I'm going to jump in here, even though I don't own DVC and wouldn't. But I do go to WDW pretty often and I do eat in WDW restaurants while I'm there. And I never have the dining plan. Ever. If I bought it, WDW would probably put up a plaque in my honor, since I normally spend far far less than any of the dining plans even though I often have one TS meal/day during each trip.Right. The experience is better overall because the negative associated with the out of pocket cost is removed. It's not that prepaying something magically makes a bad experience amazing. Plenty of people have bad experiences with DVC and the dining plan and don't return to those places. Well said.
But to get to my point--when I go to a restaurant, even a restaurant at WDW (and call me crazy if you want to), I expect to pay for the meal I'm having there. I mean, that's part of the experience of going to a restaurant. Someone else makes the food for me and I pay them for making the food, serving it, cleaning up, etc. So I don't have to. Paying for it in advance, or, in my case it'd be overpaying for it in advance, wouldn't make the meal any more enjoyable to me. In fact, it'd be less enjoyable the moment I realized that I'd paid far more for it than I had to. And it'd be less enjoyable (to me) when I realized that I was limited to certain menu choices--for example, not being able to have an appetizer as my main course--because of this dining plan.
If the co-op I live in sent me a letter saying that I could pay the total amount of my yearly maintenance in advance and that it'd be 20% more than the cost of paying it every month, but I'd be so relaxed because I would no longer have to send them money every month but could send it to them all at once, I'd turn them down. And I'm guessing that everyone who got such a letter would turn them down as well. To me, that's how the dining plan plays out. But I'm not a family of 5 who goes to a character meal every day. I believe that's the type of traveler for whom the dining plan may make actual sense.
In the same way, there are travelers for whom buying into DVC may make sense--of a sort. But buying DVC is largely an emotional decision. And a great big financial commitment.