I feel that I'm gonna be repeating what a lot of people have said, but yes, it really depends on what you're looking to do, how many people you're feeding, what age they are and so on.
I work in the travel industry so we're mostly taught to swear by the dining plan - I mean, any job that has a sales aspect tends to have the motto of 'upsale, upsale, upsale' (Even though I work in a call center and don't make commission

)
When I went last November, we had the
free dining plan, so we took it. We didn't really stop to think about it, because I mean, it was free. I was also convinced at that point that the DDP was perfection and *had* to be purchased

(what work trainings will do to you..)
Now that we're planning to go again for 7 nights in May, which is a time of year for which the free dining plan basically does not appear, we calculated everything through the menu info on allears and wdwinfo. We're going as a group - 10 of us, all adults. We budgeted for 2 meals a day, one QS and one TS, like the DDP offers. From what I calculated, we established a food budget of 375$ per person. That can cover the two meals, one or two snacks a day, some drinks (a lot of us drink mostly water, so to be fair we didn't include much of a drinks budget) *and* in most case, tipping (which for many meals will be a mandatory 18% since of our group size), which is not included in the DDP.
Between doing room only plus that food budget, and a package with the dining plan, it's less expensive to pay for food OOP for us. To be fair, we are also hoping for a room discount, which from what I can see from the past few years seems to happen for May travel dates
We did also look into splitting some meals - something else you don't worry about when you're on the dining plan. A lot of food was wasted last time we went. This time around, we'll be splitting some things, so hopefully there won't be as much waste

Mind you, that's us though - the guys we're bringing along might feel differently
All in all, it comes down to the numbers. If you want to do a lot of character meals, or some signature dining, the DDP might easily pay for itself that way. And then, if you love planning and lists and such like I do, adding it all up will just be another fun part of your trip planning
