I thought it was fun to use!
We have used free dining twice and it was very beneficial for us! I have found if you go to the character meals/buffet meals that the dining plan is well worth it! That is what we have done in the past because our family prefers the variety of the buffet. I have tried by hand using AllEars pricing oop. I have found it could work, but it really depends on what you pick. I have liked in the past that the food cost has been taken care of and has been a great deal for us in the past....
But we have been to a lot of character meals and I am thinking about shaking things up a bit... I have read quite a few peoples views on why they do OOP, it has gotten me to think, especially with the fact that we haven't been since 2008. Alot of people have said A LOT has changed since the early years. The very first time we had free dining was the first year in 2005. It was AWESOME!!!!!
That was when you had the appetizer, entree, drink, dessert and tip included!!!!! We all felt like kings and queens on that trip. If you ask the kids about Disney they will mention they loved eating out!!! That was a rarity for our family. In 2008 it changed to like it is now pretty much. We still did a lot of character meals and it was cheaper for us. We liked it, but it was not the same as in 2005.
The OOP people have gotten me to think about how our family likes to eat. Well we miss the appetizers, and the desserts in 2008 were not as good as in 2005. Alls we drink at home is water mostly. So I started playing around on the calculator. In a 7 night stay if we only went to two buffets the rest were like the regular dining plan(TS, CS, snacks), but we bought appetizers and drank water instead of soda, ordered smoothies and or milkshakes for 1/3 to 1/2 the places(because we like them!) did not do desserts because we were full from the meal and milkshakes, but saved them for in the parks (2 per person per day-counting on $10/day/person, so we could order anything we wanted) We saved money. It was a while ago I did it, but I think it was a savings to do OOP by $100 or $200 and the best part was instead of thinking the Free dining plan was the best we applied a 30% room only discount, got our tickets through I believe Undercover something through Mousesavers and customized our food eating habits to what we would prefer seems how the original dining plan nixed the appetizers and better desserts that always made us full, so we didn't care if we had our snacks. It was fun to use the calculator to try different plans and see what we liked best. We liked customizing our own plan to our eating fancy! Which meant OOP! BUT if we decided to have mostly character meals then I believe it was cheaper to stay on the free dining plan, but then we were restricted to what was at the buffet. They seem as if they are all becoming the same. It seems to be hard to get as much variety. You really have to scour the restaurant menus.
Have fun with it and think out of the box. It might surprise you what you really want.