April 9 to the 14th we were at OKW. We had our 1 bedroom villa, and we purchased the dining plan. We purchased very few groceries. Bottled water, fruit, cereal, milk and juice. We only ate breakfast in the room. We never cook anyways, but we usually have fixings for sandwiches and some heat and eat type of foods in the room.
The plan cost us $434 (2A, 1C) and when I totaled the receipts for all of the food we ate, it was $714. It was a lot of food, but even if we removed appetizers and dessert, we still came out ahead of the cost of the plan. Just twice did we bring leftover food back to the villa, but I ended up throwing it out the morning we checked out. Oh, except for the piece of cheesecake! That I ate!
DH was skeptical about the upfront cost, but when he got on the plane to come home and realized he had almost all of the cash he came with, and that we ate almost $290 more than we paid for, he is all about getting it again in the future. The only downfall I had, was being committed to our PS times. We take a very laid back approach to WDW and being on a schedule for meals was a little frustrating, but the food was so good!
I don't see how you can go wrong when a filet mignon at Concourse Steakhouse is $28.99. That meal alone you exceed your expense. The portions of the table service meals at many of the restaurants we ate at were not huge. The above mentioned steak was 7 oz, and the side of potatoes was about ice cream scoop size.
We were very happy. Have great trips, both of you!