I completely agree with you that the "upgrade" is worth it. In January, we upgraded from free
DDP to DxDP and we loved it! I had analyzed our tipping point (the point where it seemed the OOP was just as much as the upgrade), which came about because we had planned to have TS dinners every night for 5 nights, but we also wanted to have 2 TS lunches (Yak n Yeti and 50's Prime Time), 2 character breakfasts and one 2 credit dinner (Cali Grill) AND because we often order appetizers, because they're fun and because we're hungry. I did the math and it seemed to make sense. It completely worked out. We had so many delicious meals and I don't think it really took much longer than CS--all of our meals were an enjoyable break. We were able to have Kona for breakfast, Rose and Crown and Marrakesh for lunch and the previously mentioned lunches and character breakfasts in addition to our planned dinners.
We had an all snacks breakfast at Main Street Bakery, which was our plan to save credits for Cali Grill. And we did have CS twice, once for a quick breakfast and once for lunch--our first lunch of the vacation, at Cosmic Ray's, where the cast member advising my confused DH as to what he could get said, "Oh. You're the first deluxe dining plan we've had today." It was 12:30 p.m., and that was the moment that the plan *clicked* for DH and he realized why I'd been advocating for The Wave instead! After that, he was totally with the program and started scouting out TS for lunch.
One difference for us may have been that because it was January, it wasn't too crowded so we were able to make a couple of last minute eating decisions. We did have ressies, though, for most of our meals.
And, I am totally with you on the vacation/DxDP theory that it's vacation and part of the fun is the splurge and having all the goodies that you might want.
Love the trip report so far and look forward to the next stage of your vacation!