I fail to see where anyone has ever said that the "free" dining offer is always going to be the best offer available for everyone. I don't think there's any dispute that it varies by the size of the group, level of hotel, level of dining, tastes of the guests, ages and appetites of the guests etc. Last year, I went with 3 girlfriends, spread across two rooms, for 8 days. We would have had some TS meals anyway, and we came out way, way ahead on the dining plan, even with upgrading from DS to DDP. I'm going solo in December, and I figure it will be about a wash...I might come out a little behind, but as PPs have said, the knowledge that everything is set and paid for NOW is worth the minimal (I'd say less than $20 over most of 4 days) difference. My husband and I took our then 17 year old son a few years ago, because I said at the time, it's the only way we could afford to feed him. We came out ahead that year as well, though not as much as with my girlfriends (different "free" plans at the time). I've taken plenty of trips without "free" dining, and done just fine...maybe 1 TS instead of daily, maybe Ponderosa some DTD day instead of eatting at a park.
For the above example, with the $45 military discount being so much better than the $85 rack rate...with the example of my husband, me and 17 year old in the $45 room, we'd be spending far more than $40 a day in food for the 3 of us (we probably could have spent $40 feeding just DS some days.....
) For other folks, I'm sure the thought of spending $40 a day on food for 1 or 2 people is inconceivable. If it was DH, me and a 17
month old, then yes, the DDP wouldn't be worth it (QS maybe).
Disney markets this because they are trying to get people to stay onsite. If you take ME and have the dining plan, every penny of your vacation fund will be spent on Disney Property, and that's what they are aiming for. If you (general public-excited over the discount "you") don't look into the prices, ADRs, and realistic dining style of your party, Disney doesn't care; the same way they don't care that you get to the MK and wonder how to get to the Harry Potter ride.
They've got you, they're got your money, and they hope and expect that their customer service and the magic of Disney will bring you back again....at which time, you will not have looked at the prices on a menu yet (because it was all "free" last time) and will purchase the DDP without a second thought.