I was "introduced" to the "original" dining plan (there was only 1) back in 2004 I think (not sure) when they released the first "free dining" packages (at least that I remember..a lot of buzz on the boards back then).
Going from memory only, I believe the cost was around $30 for adults & $12 for kids. This plan included appetizer, dessert & tip. I got it free for our stay @ POP and it was FANTASTIC!!! Now..that being said, of course it was free and back then we could get reservations at pretty much every place we wanted (including CRT on Halloween night). We did a LOT of character meals and fine dining (Le Cellier was only 1 credit). At that time we were 2 adults & 2 kids.
We continued to get Free dining for the next 3-4 years or so and it was a great deal. During that time they took the tip away which diminished the value quite a bit in my mind.
I haven't done the DP in several years now and reading the boards am hearing that it is now $50 for adults and you only get dessert not an appetizer??? OK, that just seems ridiculously high to me for what the program offers.
However, if you are a family of adults & kids that love character meals and would do the more expensive meals anyway, I can see the DP being a good deal. I don't even want to know what the DDP costs
I do love dining at WDW restaurants, but we've been to all of them..literally every single one so the draw of doing them again isn't as high a priority to us as a family as it once was. The time it takes to do the dining is another thing that people need to take into consideration. For us, we like to do other things and we cook in our villa.
The cost for my family of 3 adults (2 teenagers) would be roughly $150 per day (if I'm calculating correctly) for 12 days that would be $1800! My grocery budget for that same time frame (including ingredients for home cooked meals, frozen "on the go" foods, veggies, fruit, chips, snacks, bottled waters, etc) is $300. My budget for the 3 Disney TS meals we enjoy is $225. Our "snack" budget is $150. Our dining out (off site) budget is $200. Our total "non-Disney DP" spending is $900. That includes Disney meals, offsite TS meals and plenty of snacks. Saving almost $1,000 and not using the dining plan def works for our family.
Draw backs in my experience using the DDP is below. I would double these experiences when considering the DDP..but this is just us.
-Time it takes getting to and from restaurant can be substantial (hours)
-The amount of food is INCREDIBLE!! We felt like we were ALWAYS full!
-We had tons of snacks leftover on the last day of our trip
-We had lots of CS left over at the end of our trip (skipped meals because we were always so full!)
-Ended up paying for a family of 5's meal @ Earl of Sandwich..I'll never forget the look on the dad's face when I gave it to him
-We found our schedule very rigid in order to make all our ADR's (I much prefer eating when/what we want and not worrying about running from here to there by such-n-such time)
The convenience was great, and that is one definite plus. Just for me, not worth the price or time it takes to get the full value of it. Just my .02