Last trip we did the dining plan and had my parents along (Dad has celiac's). They did the deluxe dining their previous trip, but we mostly ate at different restaurants. (The only ones that were repeats for him were Tusker House and Mama Melrose, so those must have been good if he wanted to do them again)
We did a few meals separate from them, but together we did:
- 1900 Park Fair (both breakfast and dinner)
- Tusker House (lunch)
- Le Cellier
- Coral Reef
- Teppan Edo
- Ohana (dinner, they did breakfast last trip and hated it)
Places he ate that we didn't:
- Crystal Palace (dinner)
- Mama Melrose
- Boma
A chef came out at each restaurant to discuss the menu and offer additional items that could be prepared. (At buffets, they also walk you through). They were all helpful and accomodating, but his two favorites where they seemed to go above and beyond were
Ohana and
Boma (they even prepared a special 30th Anniversary dessert plate for my parents that was GF

)
One note, my parents also had a lunch reservation at GF Cafe (we were at Sci-Fi that day), but when they got there and looked at the menu they felt that there really weren't any options that my dad wanted to eat. They wound up leaving before ordering and were given a reservation for Boma at almost 9pm.
His only previous trip he also tried: Raglan Road, H&V (lunch), GF Cafe (for dinner), CP (breakfast), Akershus (breakfast), Tutto Italia, Tony's, Le Chefs, Chef Mickey (dinner), and Cinderella Castle (lunch). He did specifically mention enjoying Tutto. I believe most of the buffets he just did because they were taking my 3yo niece and she wanted to meet the characters.