I think you raise some very good questions and ones that I've asked myself too! I would love to get the Dining Plan (we're renting points for BWV in October) and thought I'd jump at the opportunity but on second thoughts (or more like 3 months of thoughts!) I've decided it's not for us.
We would never eat 4 appetizers, 4 entrees and 4 desserts - absolutely no way!! More like 1 or 2 appetizers to share between us (there are 5 of us, incl. a 2 year old), 3 to 4 entrees and 1 or 2 desserts to share. We would never have dessert after lunch or, at most, perhaps we'd get a portion of chocolate cake to take a bite each out of just for the taste (I love chocolate!!).
So as much as I love the idea that you could go a bit wild and eat at more expensive restaurants and eat what we want, I know it's not good value for us.
We were originally thinking of getting it for one of our reservations at BWV (we have 2 separate reservations) for 5 nights and spread it out over 6 days (early check in on Day 1 and then it's valid til midnight on Day 6) but our schedule doesn't allow for that unfortunately - we are leaving early to go to the beach on Day 6. Had we been able to do it that way (spread the credits over days) then that would have been great value!!
But you see the other thing that bothers me, outside of too much food, is that there are times when we will have unforeseen changes in our plans. With a 2 year old, who knows when she'll want a nap or an early night? Even my older boys (12 and 9) might be just too tired to make an evening ADR and if we cancel, we'd have wasted 4 credits. Oh my, that would kill me!!

Honestly, I would stress about that big time!! lol At least, now that we're not doing it, I can cancel ADRs without a second thought if we decide to eat in or get a quick CS meal.
Oh also - and then I promise I'll be quiet

- one of the major benefits to me of staying in a DVC resort is the ability to cook a meal (maybe not so much in studios but certainly in the 1 bed. villa with full kitchen). Now I can assure you we won't be slaving over a hot stove for hours making anything complex but a quick pasta dish with salad and ice cream for dessert certainly appeals to me while the baby naps or plays happily!
Good luck with your decision! I found it ridiculously hard to reach a decision on it myself!
