Gift cards are not an option.
I used the dining calculator and it comes out just a little behind. So that doesn't bother me so much.
I guess what I am saying is, who has used the dining plan without obsessively trying to optimize it? Going to the most expensive places, getting the most expensive item. Doing character lunch/dinner instead of breakfast. Etc.
Okay, this is a different question that what you originally asked, so muy answer is different.
We generally us a dining plan, and we tend to come out a little ahead. We do not try to maximize the plan, have one person who will not eat red meat and a few who will often choose chicken or pasta over anything else, so the most expensive items are not the most enticing to at least 1/2 of our group.
We book a few AYCTE meals or character experiences, and generally prefer our TS meal in the evening. WE all like coffee with dessert after dinner. I know this so the whole water vs. soda thing is not part of our discussion.
I do not use the calculators, they are not accurate. I look at the menus, choose out restaurants and do some quick math that is based on my family preferences, and not based on averages.
If I did the math and did not break even, but was not atrociously behind, I would go with the plan. I would because I know my crew, if there is ice cream in the area, one son would make a beeline even if it was 1/2 hour before dinner. My DD cannot pass a Starbucks stand without considering if she wants another , My DGD and I love popcorn, sticky buns and pastry, and if my husband is along, well all bets are off.....I go DxDDP.
I know that we will use it. Only you can decide if you want to "take a chance" that you will at least be comfortable with the choice.