It works in your favor when you order pricier entrees and take advantage of the net sum of all the perks.
You figure in a day you can redeem the following: (Table Service- preferably a pricier entree, plus drink (especially if that drink is a slush or shake if offered, much better dollar value than just getting a diet coke), plus desert (often $8+ alone), one lunch entrée combo plus drink plus desert, and one snack, plus redemption of the unlimited drink cup for the resort.
The first day of my trip, eating at jungle canteen for my table service and Columbia harbor house for quick service, and a LeFou's brew for my snack, I made out good- I had $33 steak, plus $6 slush drink, $8 desert at Jungle Canteen. Also had $14 lunch quick service entrée combo, $4 desert, $6 snack item- so $71, plus the sales tax I would have paid out of pocket , and the
disney dining plan cost covered all this fully and costme a flat $61.84 that day, so it worked out well. You make out even better at character dinners- at Akershus where my adult meal was $57, plus drink, the pricing was even more. And I'm not factoring in the free resort cups and drink refills I enjoyed all week under the plan.
So the plan worked great for me with my plans. Now it might not be that way for everyone.
If you don't need to order desert at lunch AND dinner, don't need or want a table service every day, don't need a snack, or a drink refill cup, or if you would truly rather order the $17 sandwich instead of the $33 steak, then you will see the dining plan cost likely eclipse your own if you went out of pocket. Believe me, I LOVE to eat, and my stomach was stupid full the whole week, with all these big meals, deserts, and snacks. Too much so. I got all that stuff because it was all included in the plan, but I know I wouldn't have order near as much, or as expensive food if I wasn't on the plan. Heck, we almost felt forced to buy snacks because we were never hungry for them. But get them I did!
I jumped in on the dining plan, because I figured I was on vacation, and I just wanted to eat expensive entrees I'm normally too frugal to order, and those awesome sounding deserts, because why not? But, if you are a lighter eater, then there is also a cheaper (and less fattening) way to go about it, and just be out of pocket.
You just have to figure how you want to approach food during your stay and really, that is the choice you have to make when going with
DDP or not.