I can't add too much to all the great advice that's been given, but the best time of year that we've gone is the last week of January/first week of February. So not crowded, great weather, not too hot, but hot enough to swim.
Definitely get the Park Hopper - it gives you soooo much freedom. If you want to have a character meal at one park but want to finish your day out in a different park you can do that. For example, we had a princess lunch with at Akershus in Norway at Epcot but Cheyanne didnt' feel like hanging out in Epcot for the rest of the day, so we went back to MK. Then after that we decided to go see the Lion King show in Animal Kingdom - gives you lots of freedom to move around!
The first time we went we got the full dining plan of 3 meals per person per day - we had several meals left over. From then on we have gotten the quick service plan, which gives you one sit down meal a day (character meals), one quick service meal a day, and one snack a day - we use all those but never feel that we need more. I bring granola bars and water bottles in a string pack that we take turns carrying on our backs, along with sunscreen, wipes, ibuprofen and excedrin (we're both prone to headaches in the heat). I also bring breakfast foods to keep in the hotel room - pop tarts, cereal that can be eaten dry, PB and bread. That way we save $$ by not eating breakfast in the World. We also strategically plan our character meals to double as a brunch or a lupper (Lunch/supper) by having them at 10-10:30 in the morning or around 3 in the afternoon.
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