I think I'll take the suggestion of going through menus and figuring out how much we are likely to spend to compare. I also think there is some value in just knowing its all paid for ahead of time, but not sure if that's enough to make it worthwhile.
Understand that Disney is on 43 square miles. There is no cheap food, across the street or anywhere. It's my experience that if you pay beforehand, it doesn't hurt as bad. Unless you want to put food in a backpack, get the dining plan.
As an AP holder, I go to WDW several times a year and used to always get either the DDP or DxDDP. I used to be a big proponent of both those plans, until I went one trip without it. I like to save money as much as anyone else, but when I'm on vacation I don't want to look at prices, so don't. I order exactly what I'm in the mood for at that time. The reason I decided I didn't like the DDP, is that subconsciously I found myself trying to get the most out of it. I noticed this one night, when we were dining at Via Napoli. I really wanted the pizza, but that did not seem like a good deal with the DDP, so I ordered the seafood pasta. While my pasta was very good, every time one of those pizzas got carried by, I wished I had ordered it. It made me realize that I was subconsiously ordering the most expensive items, just to get the most out of the DDP. Since that trip, I have paid OOP (except one trip when I took my GS down there and wanted to do alot of character meals and we did the DxDDP again). I've found that I spend less money than the DDP costs and I get to order exactly what I want, whether that be a cheaper entree like that Via Napoli pizza or the more expensive steak and seafood entrees. I can order two appetizers if that's what I'm in the mood for, or an appetizer and entree, then skip dessert, or sometimes we'll order all three courses. It just depends on what I'm in the mood for. One of my favorite meals are the tomato/mozzarella salad, mussels, and cheese plate at Flying Fish. If I was on the DDP, I wouldn't be order to order all three of those at the same time and would be forced to order an entree I wouldn't even want. I have the same problem at California Grill and Jikos. I actually prefer their appetizers over their entrees. I don't care for desserts at most CS restaurants, so would rather order what I want, then go to the French or Norwegian bakery or the German candy store and order the dessert I'd rather have. I may get one of the waffle sandwiches at Sleepy Hollow, but then want to go get a Dole Whip for dessert. Paying OOP, I can order my favorites and consistently the amount I spend for the week is less than the DDP would have cost me, yet I still eat all my favorites, including steak, seafood, appetizers, and desserts when I really want them. Again I refuse to scrimp on vacation and order exactly what I really want, but still spend less than what the DDP costs.
As far as having it prepaid, once they took the tips and appetizers away from the DDP, we bought Disney gift cards anyway for those, so everything would be 'completely prepaid'. Now I just look at the menus on AllEars before each trip, figure what we'll probably eat, add 6.5% tax, and 20% gratuity, and then add a little extra for anything else we might want to buy and buy the Disney gift cards ahead of time. That way everything is totally prepaid, I never look at the prices, so order exactly what I want, and I always have some left over on that gift card to use for the next trip. I love having everything 'completely prepaid' and coming home with a zero balance on my credit card, plus extra money for the next trip.
