LOL at you still calling it FREE Dining... Sorry I just see so many people say "it's FREE" after they pay X amount of money... I am going to disney in August, and my TA told me that the Dining Plan is "GREAT" and I should do it. I did a ton of research and for 2 adults and child under 3 it would cost us $1100 for the 10 days (9 nights) which works out to $61/62 a day per person. I then researched some of the places i wanted to eat and meals were in the range of $20-$35 Quick Meals per person at most were $20 and then a snack maybe $5 (Which at all the high end prices) it would be $60 a day.
In the end I find it is not worth it for my situation, I did like the fact i could pre-pay my food but... you still need to pay the tip, which to me defeats that purpose.
To make the meal plan worth the price. You need to order the high end steaks, seafood etc... at EVERY place you eat, You have to eat a desert everywhere. and you must order drinks every time. If you don't do these things then you "wasted money" Right now I have over $800 rewards $ on my cc. Once i go to disney I am just going to charge all my meals on my CC. when i get the bill at the end of my trip, i am just going to pay my CC with all of my reward $$'s. Same thing is pre-paying but it will cost me less, and I am not restricted to ordering specific items. (I like to eat chicken or pasta or even a pizza once in awhile and not eat fancy high end meals 10 days in a row.)
My wife and I drink water (which saves us $3 pr person, we want the freedom of ordering an appetizer and then skipping desert if we are stuffed, without feeling like we are wasting our money (or skip both and save 10-20 total). Then a lot of the places i want to eat take up 2 table credits.. which would make me go through it in half the time, if i want to do Hoop-de-doo review, aloha dinner, Cinderella's Royal Table, etc...
Although for you it may be worth it, Other than when you go to a Buffet, they will charge you a meal for her even if she doesn't eat much. but when eating at a regular restauraunt you can save a meal every so often and use them to do the 2 table service credit places...