We just got back from a week at WDW. If we had done the dining plan (holiday pricing) it would have cost us $1499 plus tips. So we skipped it. Here's how it worked out.
Pro #1: I wasn't so worried about "getting our money's worth" as I had been before. My kids both got appetizers at Sanaa instead of entrees, and when my daughter ordered a salad for an entree I didn't freak out. Ordering an appetizer or skipping dessert at lunchtime was OK.
Con #1: We actually went from the 6 table service meals we had booked to only eating five. We canceled a few while we were down there.....after our first night buffet DH decided he didn't want to feel that overstuffed again and we canceled Boma, but replaced it with Sanaa. We canceled Narcoosee's, which is great when it is on your DDP but way expensive when you aren't. We relied more on healthier CS choices (earl of sandwich, wolfgang puck express) and snacks in the room.
Pro #2: we were way more flexible. We decided to eat at a couple of places (counter service ) we hadn't before and as I said before, let the kids get appetizers for their entrees if they wanted to. One CS meal my son was feeling a little off so he didn't eat at all, and I wasn't mad about it. We also did not eat as many snacks!
Con #2: a couple of times we had to explain to a snack cart CM that no, we were not on the dining plan. It seemed to confuse some of them.
So all in all, it worked for us. We spent less money and ate less food. Of course the kids are 13 and 17, so we don't have to be uber planners about meals like we would have been when they were little. But then just a few years ago the plan was $40 pp and included tips!
I'm glad we tried it and I don't think we'll be using the DDP for any trip soon, especially the way the price is going up.
Daisyx3