Ever since we did the deluxe dining two years ago, I think it's so worth going during free dining and paying for the upgraded dining to deluxe. We just booked October at Wilderness Lodge with free dining and we added the deluxe dining.
If you space your meals right, your covered perfectly and never hungry, while getting to try food from so many places. We usually do a 9 AM breakfast, 3PM late lunch and a 8-9PM dinner. It gives us enough time to be hungry for every meal and not feel like a cow when getting an app/entree/dessert each