we've been to the Wilderness Resort 6+ times just about once a year (we were just there this past Jan I did a mini trip report in my PTR for Disney)
anyhow I agree with most on the food expense in the resort. Bring from home for breakfast and lunch I could not stress that enough! they have a fridge and microwave in every room, plus in some an extra sink and counter space. We do breakfast in our room, usually cereal, fruit and muffins or peanut butter bread. Lunch even though they say don't bring food, etc into the waterpark areas we always do. Just not overdoing it. I usually go back to the room, make some sandwiches and bring them back to our table. The fast food areas in the wp areas are very VERY $$$$$! Only do in an emergency.
As far as eating dinner, we've ordered pizza to the room, have done the buffet meal where younger kids eat free w/ adult purchases a few times. We've also eaten at the Survivors Bar and Grill above the waterdome...fast service and pretty good food, can't remember for sure the cost but a little above average I believe. My favorite place to dine in resort is the Thirsty Buffalo Saloon (you can order to go too) by the Wild West Area. I think there prices are basically reasonable and if you go at the right times it's not crowded. We've shared plenty of kid meals too.
Outside, the New Monk's bar/grill right by the Resort was real nice. I had a pulled pork sandwich w/ those crunchy onion straws on top. Delicious! And we've been to the downtown joint too. The kid meals are served on Monk frizbees. We've eaten at Moosejaw several times too, but usually a big group so we've always sat downstairs. But we like it there, but crowded!!!
Hope that helps. feel free to pm w/ any specific questions about other things too.
Hope you have a great time!