We also just eat wherever we want, whenever we want. If we want to eat at places where the
ddp made more financial sense, we'd buy the plan, or if
free dining was offered, and paying rack rate for a room made financial sense to get free dining, we'd pay for it.
Do the math for your family to make your decision. It's pretty cut and dried if you should get the plan or not. Factor in your own convenience factor, as well. IMO, swiping a credit card is just as convenient as scanning a magic band. I will pay up for convenience of other things in life, so I understand the convenience factor and not wanting to think about meal prices - I totally get it. I just don't agree with it for WDW food, but I do the same thing in other situations.
Paying OOP, I think decent bargains for the quality are:
Flame Tree Spare Rib Platter - easily splittable for two people, imo.
Kimonos for Sushi
Hot Subs at Fuel - VERY high quality. I was extremely surprised.
Teppan Edo (food is just ok, chefs' "shows" can be great - all in all, worth the price, imo)
Hoop De Doo (isn't HDDR actually cheaper, OOP?)
Trail's End
If you hapen to be near Swan/Dolphin around a meal time, consider those options. They are routinely mentioned in the "Best Restaurant" threads. I find them to be better priced, and better quality - probably since they are not Disney owned.
My deal, in a nutshell is this:
The food at WDW, in general, is overpriced, and haphazard in quality, although, for the amount of ppl they are feeding, they do a very nice job compared to other theme parks, for SURE. I live in a big food town, so WDW food is not a major focal point of our vacation when in Orlando. I definitely do my research on where to eat, but I'm mostly looking for stuff that is decent without being too overpriced, and factoring in that walking around in the heat and going on rides, stuffing ourselves isn't optimal.
Do the math, if you are still doing multiple character meals, or if your family dines the way the meal plan is set up, the DP might make more sense for you to save money.