I'm all over the place with the dining plan. I did it for the first time last year, just to try it. I stressed about it the whole time because I'm the type of person who *has* to ensure that I get top value you for my dollar. In my case, there were nights that I wanted to order the chicken, but when it was the cheapest thing on the menu, it made me feel like I was getting ripped off (and I was).
I guess I differ from a lot on this thread who are locked into a food budget and are stressing if they go over. I am pretty frugal in most area of my life, but my DH and I do make good money, kids are out of college and the house now, etc and I don't need to adhere to a budget so much. One reason for that is because, as I said above, I'm pretty nuts about getting good value for every dollar I spend: be it clothing, food, cars, etc. With the dining plan, I really worked that thing over every day and spent a lot of time stressing. But, I will say, on the days I "got over" on the plan, it was an exhilirating feeling!!
We're going again in November and I probably won't get it. On the last trip, there were things some people wanted that were excluded (mainly the beer, wine, or mixed drink flights).
As far as the ease, I just link my credit card to the band and pay that way--just like with the DDP. I also link my older kids so when they are separated from me, I'm not having to worry about how they'll pay for food.
Then, I like the fact that I can charge my meals to a credit card that has a good percentage rewards back on dining out. I realize that when I charge my room and DDP, I also get rewards, but I can shift my distinct dining costs to a card that specifically favors dining so in that way, I get a discount on my food.