We are doing the dining plan in August because it is "free"; of course I am paying an outrageously higher hotel cost to get the "free" food. Basically "upgraded
free dining" means DD and I can eat at WDW for $50 a day for 2 people. Going during free dining means we will get to try many restaurants we've only thought about, like Teppan Edo, Brown Derby, and Chefs de France, but that I know won't fit in the "$25 per person per day" scheme (if we were paying oop)

. We have been to Disney many times and DD and I have three "must-do" table service restaurants: Boma, Crystal Palace, and Kona. I did the math and discovered that the cost of a cheap value resort room ($58 a night) plus dinner at these 3 places, plus 6 more days of meals, would be more than the cost of "free dining" for the two of us.
However, while it makes sense financially, I am not sure it's really the best plan for us, food-wise. We are not dessert people

, especially at lunch, and we rarely order soda while at WDW (or anywhere else, for that matter). I am already wondering if we can get fruit substituted as dessert, and will bring a couple of tupperware dishes to transport desserts back to our hotel room (although the thought of cheesecake for breakfast... well...

) We are looking at "free dining" as a chance to explore new restaurants and are basing this trip around our meal plans. Usually we are better off paying oop for our meals, but this trip we will be adventurous! We are actually pretty psyched about this opportunity
BTW, just because it says "counter service", don't be misled into thinking you would eat burgers, fries, and nuggets all week! There are some amazingly good meals to be had at Disney's counter service restaurants!