Well, in your case you would have been paying $97 more per night for your room. The dining plan costs $37.99 per adult (age 10 and up) and $9.99 per child (ages 3-9). You can pay those costs to add dining to your $259 rate, so basically if you have two adults and two kids, it's pretty much a wash. If you have just two adults, it's cheaper to pay for the dining plan yourself. IF however, your kids are over 10 years old and therefore charged the adult price for the dining plan....you'll save money. Of course, you also have to buy at least one day ticket for each person, but except for Annual Pass holders, you'd have to have tickets anyway. So you really have to run the numbers for your family size. And of course the value resorts are like $100 a night with
free dining.....so that might be a bargain IF you don't mind the tiny rooms.
Now...the rub for me is that the free dining is only in August/September....frankly a totally miserable time to be in Florida's dripping heat. And let's not forget about the crowds too.....read the boards a while and you'll realize that getting an ADR for even the unpopular restaurants is about as easy as winning the Lottery. And let's not forget that all those ADRs which equal capacity filled restaurants also mean very long lines for the rides and shows and just standing around.
Personally, even with two kids considered adults, I'd rather go during an off season when the lines are shorter, the weather is more pleasant, the crowds are lighter and I have a fighting chance to get a few decent ADRs. It may cost more, but I'll get more rides in, more shows seen, and less frustration waiting in crowds. Heck, for some people they could just go a day or two less, spend the same amount of money and still get the same amount of things done because it's less crowded....and have a little more magical time with less stress and frustration (I'd probably still go the same length, lol). But then again, I'm not a crowd person for any reason.
The ones I really feel sorry for though, are the ones going during free dining but NOT getting free dining. Maybe they didn't know about the promotion, or they didn't get in on it before it ended....or the free dining rooms were all sold out.....whatever reason, they're going to have endure all the negatives of free dining season and still pay for their meals.