To the OP, great post. This has generated some great comments.
I have debated this issue with myself for weeks. We are DVC and the plan is available to us in June when we go for two weeks. We have two adults, two hungry teenagers (boys that really enjoy eating out), a preadolescent who is considered an adult, and a seven year old.
In the past we have always had cereal in the room for b-fast (maybe one character b-fast per vacation for the kids), a table service lunch (cheaper than TS dinner for OOP although the menus are usually limited, and a counter service dinner (we call it dining around the world -- we just cruise around world showcase letting each family member grab a CS meal wherever they want although they usually don't get much further than the fish and chips place in England). We have also had the luxury of a full kitchen and usually have a number of meals in the room.
This trip we have decided to eat out more and I kept on salivating looking at the dinner menus for TS restaurants on Deb's website. Dinner is more expensive yet we would really like to try a few of the restaurants in the evening (Coral Reef, Brown Derby, Tony's, Le Cellier, Concourse, etc.) I did the math having more TS dinners rather than TS lunches and it made more sense for us to do the dining plan this time around, so we're going to give it a try. We plan on salads for appetizers for the most part, which we usually do anyway, the entree, and then carrying out the desert for later if we aren't hungry enough for desert at the time.
My sons are really looking forward to having access to snacks without pleading with the holder of the wallet (me), and they are also looking forward to having beverages with their meals (we have always had water with meals to save money and they think I'm a royal tightwad and routinely tease me about it as they get older -- this will prove to them otherwise.) My wife is looking forward to not dealing with buying groceries and preparing meals, and we are all looking forward to not having to haul groceries into the room.
For a two week stay, the dining plan will set us back quite a bit, but it won't be much more than being on the "dad's dining on a budget plan" when we consider the number of times eating out we have planned this time around, which is at least 1 - 2 times per day for the duration (so many restaurants, so little time). I'm going to look at it like an all-inclusive, pay for the plan, and then just try and relax and enjoy watching my teenagers and their mom enjoy their chow, and of course enjoy my chow along with them.
It stinks paying adult price for the 11 year old, who will likely want to eat from the kids menus most of the time, but it still works out financially for us, especially if we can pay for a few of those kids meals for the 11 year old OOP, if the restaurant will let us, or share a few meals with him if he can find something on the adult menu that he might like.
This is our last family vacation before dash-one son leaves the nest, and for this vacation I think the dining plan will be the way to go for us.
I too am glad to find that not every one is going on the DP. I was beginning to think I was a loser for even considering not going with the DP. I'm glad to hear it doesn't work for everyone, because we were right on the border of having it not look like the best way to go for us. The dinner TS cost for OOP is what tipped the scale for us.
The boys are going to love having real beverages at every meal. Does it sound like this dad is trying to purchase their admiration?
Sorry for being long winded.