Of all my trips to WDW I have never purchased the DDP. Never found it to be worth it and always felt like it just wasn't as flexible as I'd like it to be. Typically I prefer to grab-and-go for breakfast (parfaits, bagels, etc.), do counter-service for lunch, and table service for dinner... though not always.
The BF and I are starting to think about a 2016 trip and his mom absolutely insists that the DDP is the way to go.
I know it's a hot topic and the right answer is probably different for everyone, but I can't help but wonder if I'm missing out on something great.
So my question is this, what sells you on the dining plan? Is it convenience, value, or something else entirely?
It is true that it's good for some and not good for others. I'm curious if your BF's mom has used the DDP in the past few years. If not, she may be surprised to see how much it has changed. For example, 10 years ago the DDP included appetizer, entrée, dessert, non-alcoholic beverages and gratuity. Yes, I did say gratuity! You truly had to pay nothing when you went to the restaurant. Then they began taking things away. First it was gratuity (except for dinner shows), then it was appetizers, then several locations began opting out of the program, then they started increasing the cost of the plan based on the time of year you visit (holidays and summer were more expensive), etc.
Keep in mind, 10 years ago the DDP cost approximately $35-$40 per adult per day for the basic DP (1 snack, 1 QS, 1 TS) and now it can cost $60+ per adult per day. You pretty much have to get the most expensive entrée and dessert for every TS meal to have a chance of breaking even.
It also depends on how you like to eat. Are you a dessert person? Do you sometimes like to just get appetizers instead of an entrée? Do you drink alcoholic beverages?
I know that this does not really sound like a response from someone who is sold on the DDP, but at one time my DH and I were sold on it and we would get the DDP for every trip. Unfortunately, though, at some point it began not to make sense for us. We now use TIW. It covers most TS restaurants and is a straight 20% discount off your entire bill, including alcoholic beverages. (However, I believe the only QS locations you can use TIW at are the resort food courts.) If that is something that is available to you (if you are FL resident, DVC, Annual Passholder), I would strongly suggest that option.
Otherwise, I would really take a look at the menus for the restaurants you plan to eat at and see what you might order, add up the cost, and see how the numbers work out for you.
Hope this is helpful! Enjoy your trip!!!