We went in early June with our 2 1/2 year old and very rarely bought her a meal. I think we did once at TS, and maybe twice at CS, but we had extra CS credits for that.
With four people ordering appetizer, entree and dessert, there was always something my extremely picky eater could eat, We did two buffets (CP & BOMA) and two family-style meals (GG & Ohana). At the family-style meals, they did bring out children's options for her even though the rest of us were considered adults. Only once did my DH make his decision to get something to share with her, but that didn't even end up being necessary because she liked the veggies that came with our meals best. We also shared the skillet with her at WCC.
We ordered her a milk at every TS, and only once were we charged for it, but I think that's because we ordered her her own dessert, too (at Alfredo's).
We often ate out CS at Pop, which was great, because there is a lot of leeway in the desserts. Many times DH or I would get her fruit as our dessert credit. It was a nice big plate of it, too. Add in some of our food, and you've got a good meal.
Have fun!