He is ONLY FREE if it is a buffet or character meal. If it's a sit down resturant like Shutters (Carribean Beach Resort) than you will either have to share a meal with him, or pay cash for his meal.
We didn't find this to be a problem at all. Our 5 yr old ate our food, we ordered for the 2 yr old. With the dining plan you get appetizer, main course and dessert plus drink. We often asked if they would split the kids one drink. At breakfast we had the refillable mug that we used for our drink and got hte kids drinks then. So, you could pick up 2 juiceboxes and bring that as the kid's drink at a sit down resturant.
Nora