I think it depends on your age and eating habits. We have just returned from our trip a few days ago, we're late 50's and we do not have any chiodren, all grown. From past experiences we know the meals at WDW are huge, we do not eat alot while on vacation, bloats ya and slows you down, so we never used the dining plan. We also don't like to be tied down to dining times, pre-scheduled, screws up our day knowing we have to be here at such an such time. We enjoy counter service more than sit downs, have a couple of sit downs but we share alot of meals. Thats about the only way we can eat 2 basic meals, portions are too huge. We look around us while eating and see so much food left by other guests its nuts, you paid for it, eat it or don't get everyone a meal, heck we could survive on what they left, hence why we're againt the dining plan, just too much food too many times a day.
Don't get me wrong, others swear by it, saves them tons of money but to me either you're huge eaters, love 3 complete meals a day or have growing children who can eat. We vivit other resorts, each has their own unique menus, even the moderates and we hit our favorites, last trip was our 39th and our dining just about stays the same. We stayed at the WL, just the 2 of us and we didn't go hungry, hardly spent 200.00 for 10 days on food, and we did some sit downs, we grocery shop before arriving and have pool picnics mainly for lunches and this give us the opportunity to have an ice cream or two and pop corn through out the day. We're not cheap but its just our honest way of doing dining while at WDW.