We are another couple that doesn't do the dining plan and we don't skimp.
First things first, I don't like having to plan what and where I eat based on a plan. Eating at Disney to me, is no different than eating at home. If I want a steak, I'll go get a steak. If I want some simple chicken fingers, I'll do that instead.
I like to eat at Downtown Disney and for dinner on our last trip, over half of our dinners were at DTD restaurants. Taking a look at the 2010 WDW Dining Guide, out of the 15 eateries listed, 9 of them do NOT accept the DDP, 5 of them being some of my favorite places to eat; House of Blues, Bongo's, Rainforest Cafe, Fultons and Ghirardelli. Those are 5 places we wouldn't have been able to eat or would have had to pay out of pocket for, and I can tell you we stopped at Ghirardelli nearly every day of our trip. To be fair, that's a very high ratio of places that won't accept DDP compared to the rest of the resort, but again it's some of my favorite places.
Other times, we might not have the time to sit down at a TS or even wait for a TS. We're very spontaneous, we generally don't decide on what park we're doing until the day before which pretty much kills any chance of being able to book a reservation at this ridiculous 180 day bit. Heck, we usually don't plan our vacations until a ~3 months before we decide we want to go!
We generally do cereal for breakfast (who wants to get up at the crack of dawn on vacation to go sit down for breakfast to be at the park for opening?), usually "graze" throughout the day on snacks or do a CS then for dinner, sometimes it's a CS, sometimes it's a TS.
When we're at home, we rarely do deserts and when we go, we share. We much prefer an appetizer which again, we share. So why would we buy a plan that includes a desert at every meal for 2 people? That's 4 deserts per day (for a couple), when we *might* have 1 when we go out for dinner at home.
I personally feel that it's just simply to much food for the average person. The last thing I want is to be stuffed to the point that I don't enjoy my vacation. A dining plan would make this hard since I was brought up to not waste food. This goes back to why we as a couple share an app or desert.
The couple that we're going with this year got the DDP last time there were there and loved it. I started asking questions why they loved it so much and it wasn't the value or selection of restaurants but simply that it was prepaid. We had a 2 hour discussion (debate even?) between the 4 of us on if we should get it again. I expressed my points, that I didn't like being limited on where or what to eat, etc.
It finally came down to me getting our room charge from our '06 trip. The total room charge bill was just a little over $1100. I went through line by line and subtracted items that I knew wasn't food (World of Disney, Summer Sands, Pinstations, etc). I left things in that I couldn't remember what they were (Fantasmic, Frontier Trading Post, Pirates Bazaar, World Traveler, etc). The total came to just over $700. To my memory, everything we ate was charged to our room charge with nothing on other forms of payment (other than tip, which was left as cash usually).
That was for a 10 day trip, so some basic math, 700/10=70/2=35, so $35 dollars per day, per person. Granted, that was 5 years ago, so I'm sure food prices have gone up a little bit, but that's still a 13 dollar savings per day, per person. Over a 10 day trip, that's $260 or the cost of one of our airlines tickets. Some other things to keep in mind, as I said there were some things on there I couldn't remember, so they were left in. They could have been pins, or other little souvenirs. Additionally, while neither of us are big drinkers, there were a few beers and cocktails included in those bills that wouldn't be covered under the DDP.
In the end, we all decided to forgo the DDP. I'm going to keep track of the receipts this year and total everything up to see if we made out, broke even or spent more than what a comparable DDP would have cost us.
Don't get me wrong, if you love to eat, don't get stuffed easily and love desert, the DDP isn't a bad plan. But it certainly doesn't fit everyone's eating styles.
If Disney was wise, they would come up with a point based system, similar to DVC. I would also go as far as saying to break it down based on what you're getting ala carte.
You would buy say, 20 points per person per day, more if you feel you need them, less if you feel you don't. Maybe a snack is 2 points, a "combo" (drink/fries/entree) at a CS is 7 points, maybe you don't need a drink or fries and you just want a burger, 4 points. An appetizer at a CS is 4 points, an entree 8. If you decide you want to snack all day long, fine. If you decide you want 2 CS's for that day, fine. If you want to do the "traditional" snack / CS / TS, fine. If it were me I would buy on the side of "short" so I didn't have leftover points at the end of stay and just pay for everything else out of pocket. Possibly more confusing than just saying "you get this, this and this", but for people like me who want more flexibility out of it, I would actually consider buying something like that. I would also suggest it be bought as a "bulk" of points for the family instead of a per person thing. Of course, that still doesn't fix the problem of non participating eateries.
To throw in another though, I think Disney is shooting themselves in the foot with not allowing 'common folk' to buy a TIW card. I'm not a FL res and right now until we buy into DVC, I won't be buying an AP. For whatever reason, Mousewitz decided that we shouldn't be able to buy them. I would buy it in a heartbeat, maybe I'll save money, maybe I won't, but it would encourage me to visit places that we normally wouldn't like V&A's or maybe make stops at Yachtsman a little more frequent. I love steak, but seriously, $42 for a NY Strip? I get a bigger NY strip that is just as good at my local Outback for less than half the price and a better strip at my local "high class" steak houses for $30. I would typically get a filet, but I used strip pricing to keep everything accurate.
My 2c.