This was nice to read. I like the DDP for reasons you mentioned (grimacing at the price of everything) but I just can't make it make much financial sense at all anymore, even though we are people who eat 1 QS a day, 1 TS, AND we are BIG dessert people. (When we go out at home, we almost always get a dessert, although probably more often we share rather than each person getting their own, but...) We ended up with "free" dining this year. There are 5 of us (4 disney "adults") and we're staying CBR, so with free dining and gift cards, it was a decent price. We upgraded to the regular plan, which was a no-brainer, because we had two absolute "must-do" meals, Norway for DD 4's birthday, and Tusker House for the River of Lights package, and just with those two meals, it basically almost cancelled out our "upgrade price". We're in a tough spot with kids age 4, 10 and 13. My 4 year old (and honestly the 10 year old) still like character meals and it's efficient for meeting characters, but man paying $50 for a 10 year old girl whose the size of a bird is tough!
Before we got free dining, I went through and basically tried to make a realistic, but generous, food budget. I did a TS with some desserts every night but 1 (2 character meals), mostly gave everyone 2 snacks a day, gave each kid their own meal, even though I think there are several times they'd probably share. It wasn't quite as much food as the dining plan, but darn close. And for $700 less than the cost of the plan. Then added that on to my hotel and ticket cost, and decided, "Yup, that's an amount that falls within the money I have saved for this vacation." I knew, logically, we weren't actually going to eat quite that much food. So in my mind I had told myself that basically I had the freedom to eat whatever I wanted while we were there, and we could easily afford it. We got free dining so I can't test my theory, but I feel like with my calculations I had done, that mentally helped give me the freedom from the worrying about the cost of food all the time. For others, having the money on a gift card may do that too!
I read your DxDP trip post too. Very interested. On a next trip I thought about maybe doing 2 rooms somewhere, and adding on the DxDP to 1 room. With the sharing allowed now, that seems to be somewhere you can still get good value!