We've gone several times and tracked our "carefree eating" while on the dining plan. After totaling all the receipts, the reality is that we JUST broke even. It was less than a $20 difference between what we paid for the dining plan and what we managed to eat. We could have spent more, but it would have required eating things off the menu that we didn't necessarily want but was priced high.
With that said, we still get the dining plan. What we also found was that we tried restaurants and snacks that we wouldn't have otherwise tried - especially during food & wine festival. $7 for ramen? No thank you. A snack credit? Sure. $28 per person for breakfast?!? No thanks, but a single credit - well it's Beauty and the Beast or Bounty Platter downstairs same "price" Be Our Guest it is! We'll spend 20 snack credits during our tour of food & wine (which also helps tremendously to break even). But once we finish all the restaurants, we'll probably stop getting the plan. There's definitely some good ones, and some that aren't worth it.