There are many blogs dedicated to figuring out the value of the dining plan, and whether it is right for you. They are highly opinionated. This is my opinion, with explanation, for what we did and why it worked for us.
If you need one site in this field, this is it. You can put in your exact plans or ideals (like "standard quick service lunch") and the program will highlight the breakdown of every meal based on average prices, as well as if you don't use a meal plan. Try it.
After using that tool, we knew the deluxe was our only option if we wanted to save some money.
Character meals, character meals, character meals. We had so many character meals booked that deluxe was the only way to cover them all or not waste erroneous quick service credits. We could have paid out of pocket, but this did actually save us about $90 in the end.
We tried to balance character meals with other sit-down meals, so that we could eat some delicious food while on vacation. The character meals are great fun and a wonderful way to meet about 5 characters in one hour. (The one time all characters didn't get to us in under 45 minutes, a cast member brought one over to our table and walked us to another on the way out. No meal took over an hour.) The buffet food is okay at best at these locations, with the exception of Akershus breakfast in Norway and 1900 Park Faire. (Those buffets I'd gladly go back to!) For character meals, you are by and large paying to meet the characters while eating generic buffet food. We disliked the food at Chef Mickey's dinner so much that we switched our breakfast on the last day to the buffet at The Wave. No characters, but the food was better.
Since we were all in, we aimed for buffets at least once a day. Our 2-year-old wasn't on a meal plan, so the buffets made it a bit easier to share. (The kid entree portions widely varied by restaurant, and we found splitting a kid meal between the two of them was usually adequate, but occasionally small. Good thing they specialize in over serving adults!) Many of the buffets are themed, with a few unique dishes. Overall the food at most buffets was pretty good.
We visited Boma for breakfast before going to Animal Kingdom. Fair warning - if you rely on Disney transportation, the busses only run 45 minutes before a park opens. You will need to take a cab if you want to get from any resort or park to Animal Kingdom Lodge 45 minutes before the park opens. It cost us about $25 to go from The Contemporary to AKL. If I had known this, I would have made a later reservation. Ah well. The food was delicious, fresh, and unique.
For our Date Night, we ate at The Wave. Our server was phenomenal, and the food was delicious. Hands-down, the best meal we enjoyed. (We also ate at Tony's - awful faux Italian food, Cinderella's Royal Table, Be Our Guest Dinner, Chefs de France - do not recommend this at all, and Liberty Tree Tavern.) If you are going to have a date night and pay a sitter, definitely go for one of the more adult meals at Disney. While on our date, we also found that the Contemporary arcade room has massage chairs in a corner. $7 and 15 minutes later, our tired backs were feeling much better! Maybe it is a silly way to spend part of a date night, but in a trip centered around kids, all we wanted to do was stay out for a few more minutes while the sitter put them to bed.
To help use our snack credits and save on a few table service credits, we enjoyed snacking around the world at Epcot for lunch. There is such a variety of snacks to enjoy at this park! Do not miss it. We attempted the same thing at Hollywood Studios because our Fantasmic! dinner was at 4:15pm, and the snack choices were few and far between. For snack credit meals, Epcot and Magic Kingdom are the way to go.
The grey stuff is actually delicious.
I don't think we would ever focus on characters so much again (seeing as our kids won't be 2.5 and 5 at Disney again), and if we opted to do a dining plan in the future, we would take it down a notch. Overall we felt it was worth it for the characters and the lack of worry at least once. We used all but one table service credit and 3 snack credits, which I had banked for Starbucks (yes! fancy drinks are a snack credit!) before realizing the line would forever be 30 minutes or greater. I love my Starbucks, but not that much. (Seriously, Disney, putting one more Starbucks in each park would do you so many favors.) We were able to get our younger daughter her own meal, using our credits, when she wanted something different, and we used 6 credits total to dine at Cinderella's. (For the record, this was a cute meal and getting into the park early was amazing, but Akershus was the better experience overall, and a better bang for your credits.) The breakfast buffets hold a good deal of value, but I can understand now why people pack lunches to bring to most parks. It was the right call for us this time, and we really enjoyed the ease of the dining plan.
We also received refillable mugs as part of the plan. Each person on the dining plan gets one mug, and you can fill them at any quick service restaurant at any resort. Every morning, I took our mugs and filled one with coffee, two with Coke, and we tried to wake up as our kids bounced around, ready for a park day. You can not use the mugs for milk, but you can use them for coffee, tea, juices, and all fountain beverages. Seeing as our kids need none of that, my husband got a bonus cup of soda each morning. All the kids care about is having a cool souvenir, anyway.
A word to the wise, eating all meals at Disney - the food is typical American food. The portions are huge, the salt is obvious, and the focus is largely meat, dairy, and carbs, especially on buffets. Even the salads were overdressed and most vegetables were laden with dairy and sodium. Beware the bloat. Seriously, bring some bloat tea or cranberry juice, bring some kale with you, something, because by the end we all looked like we were harboring food babies. Three days of eating salads and soup have us all feeling better.