I don't have any experience of the whole Disney thing hence I didn't know you could eat anywhere. Tell me more about the dining plan?
have a look at this...it lists the restaurants for the different types of dining ie counter service or table service. It lists where all the restaurants are be it in the parks, down town Disney or at the different resort hotels, and you can eat at any of them. As pp said you will need to look at booking the table service ones which is easy to do.
http://www.wdwinfo.com/disney-dining-plan-restaurants.htm
I can't imagine my son staying up until 10.30 every night but then we aren't going untill 2014. I am also overwhelmed by the choice of accommodation. There are so many pros and cons. I guess I need to list out our priorities.
There are indeed LOADS of different options. To me it sounds like you would be happier with two rooms ie one bedroom and a living/kitchen area, so maybe look at OKW or SSR, which may include free dining and have a washing machine and also look at the new Art of Animation resort which is a value resort. The value resorts have laundry facilities normally near the swimming pool so you could always go for a swim while waiting. There are of course many many other off site hotels but you won't get free dining although they are often a whole load cheaper so paying out of pocket for food may still save you money.
2 rooms or King size bed and 2 singles.
Close to the parks
swimming pool
Washing machine as we like to travel light.
Choice of eating places