I forgot about the in-room service - it is great and may be better for a child that young, so they can get a decent nights sleep. We used Fairy Godmothers - if you search Fairy Godmothers and phone number on these boards, you should be able to find the number.
We used the service on a few trips when the kids were younger - they sent the same sitter each time - a grandma - and our kids loved her. She brought with her a suitcase full of toys and books suitable for their age groups.
For the Neverland Club - i think i reserved it thru Walt Disney World Dining, when i made other meal reservations.
You are right it is difficult to choose where to eat. I still struggle after several trips. Generally, I try to fit meals around whichever park we will be in - we try to do one sit down meal a day. At least one of these will be a character meal, and one adults only meal.
IMHO the best character meal which we always do is at Chef Mickey's in the Contemporary - it is so fun and lively. My kids also love the Japanese restaurant in Epcot and always talk about the place. Another must do for us now, is Le Cellier in the Canada Pavillion in Epcot - it is very nice, especially if you like steak. For a nice meal, which is a bit more relaxed as opposed to fancy and therefore nice for kids too is Artist Point at the Wilderness Lodge - it is great, plus it gives you an opportunity to look around the lodge, which is fantastic.
If you want a hand planning, or you're struggling to decide between certain restaurants, just ask. I love helping first timers plan.