Wow, what well reasoned and compelling arguments all the way around. (And btw--i was probably being a little too cute with my post title..I know it isn't really free, it was more of a rhetorical question!)
I'm still on the fence.
Let me throw a few more things out there. The DDP plan says it is in place for the number of nights that you are staying. So, if you are staying for 10 nights, and then buy a 10 day pass, how many credits to you get? You actually are going to BE there for 11 days, but you are only staying 10 nights. So do you get 10 TS, 10 CS, 10 Snacks, or 11 of everything?
It does make a difference in the math, and lowers the "magic number" by about 10 percent.
WTP's point about "what we will eat" is well taken. I share some of those same tendencies. 1) We routinely share drinks, at least when they are refillable, in order to save money no matter where we are. 2) I love dessert, but my wife doesn't. Even when I do want dessert, I also don't always want it right after a meal--I might want it a few hours later. 3). Sometimes I like to try appetizers, and my wife loves soup. Say you go to Le Cellier on the DDP...now I have to pay $6.99 for the cheese soup. But I had it once and I loved it...but I'm not sure if actually would bring myself to pay the money for it. 4) I totally get it when it comes to certain traditions, etc. One of ours is that we like to have some nice breakfasts, like at Kona. Well, that's a terrible use of a TS credit, so we'd probably be paying out of pocket.
Here's what doesn't apply. 1) Nobody in our party drinks alcohol. 2) We have no desire to eat off campus during our stay. 3) It will be December, so I'm not that worried about it being hot. We were there in January a few years ago and it was really pleasant, we never were too hot to eat!
Now, here's a wild card. My parents are the kind of people that don't spend a lot on food. If you go to a "nicer" restaurant, they may not say anything but they will politely order the least expensive thing on the menu. At Disney, they are going to want no part of most of the table service experiences, and when they do, I KNOW they'll be sticker shocked and end up ordering whatever is cheapest. We'll be doing a lot of hamburgers, a lot of pizza, etc. Over the course of 10 days, that's going to get old.
Regardless, we'll do Chef Mickey's because everyone wants to watch the kids interact with the characters. And my wife and I will have opportunities to go have some nice dinners on our own. But with the DDP, I know they'd probably actually eat something nice for once. My mom has already said, "if we don't have the dining plan, I'm not going there" a few times in our trip planning conversations about certain places I've brought up. (Not that they neccesarily are advocating for it, she was just being honest about her mentality).
However...the other concern I have is simply logistics. I HATE being locked into needing to be at a certain place at a certain time, and I wonder how much "pressure" we're going to end up feeling trying to herd the whole clan over to restaurant x at a certain time. How badly do you need ADRS? I'm planning on making them at my 90 day window, but since the park hours for my month won't even be out yet, I really have absolutely no idea when we're going to want to go to certain places.
It was tough even the last time, when it was just me and my wife in '07. We really wanted to eat at certain restaurants, so we made ADRs...but I remember it being a pain in the butt, because we'd want to go on "one more ride" at Hollywood Studios, but instead were stuck watching the clock because we had to be at Chefs de France in 30 minutes. (Thank God we had a car, and will win this time too). But you see my point.
So anyway...still undecided, and trying to figure out whether we'd be getting 10 or 11 days credits.