I've done trips both with and without the dining plan, and we usually save about $200 by paying OOP. We don't necessarily eat the way the dining plan is set up; we mostly drink water at meals, we don't usually eat dessert with every meal, we like snacks more than once a day sometimes, etc. We've also found that with the heat in Florida, we don't eat anywhere near as much as we would at home, so the DDP is too much food for us. We were happier paying OOP.
Some things to remember if you keep the dining plan:
First, it only covers TWO meals a day. What is your plan for that 3rd meal? DD and I found that we can often share meals at Disney, so we'd use her QS credit to order a bounty platter to share at breakfast, and my QS to order a lunch to split (Flame Tree BBQ does a half-chicken with 2 sides- PLENTY for 2 people to share), then each have a TS credit for dinner. If you aren't going to share meals, you'll need to pay for breakfast OOP OR have food in your room for breakfast.
Will you want more than one snack? At MK, we always have a dole whip, but later in the evening someone invariably wants a Mickey Bar. YOu'll pay OOP for any snacks above the one allotted per person.
Do you eat desserts? The DDP includes dessert and I found most of the QS dessert offerings to be abysmal. We'd skip them or pitch them about half the time
but still want those 2 snacks at MK!
Are you planning on going to the Food and Wine festival? You can use DDP snack credits at the booths (not for alcohol), but then you have no snack credits left for your other days. Also, we have discovered that when we go to F&W, we do NOT need to eat supper that day. It's always a waste, as we are full of food from noshing our way around the World!
Another thing to consider is your park tickets. What kind are you getting, and for how many days? It's possible to save some money here. If your trip is Sunday to the following Monday, you could get away with six day base tickets. That gives you 4 single park days, plus two days of re-visit. You mentioned
MNSSHP tickets, so DON"T go to the parks on that day. Take a casual day by the pool, and hit MK at 4pm for the early party entry. You'll be able to stay in MK from 4pm-midnight, and 8 consecutive hours in MK is a LONG time, especially with the lower crowd levels for a party. Actually, if MNSSHP is your MK revisit, then you'll have 2 MK days, plus a day each at the other parks, and two revisit parks. Stretch those park days, and with basically 2 days at each of three parks, you really don't need park hopper tickets.
Remember all the free things there are to do at Disney. We can fill an entire day doing Disney-related things that don't include going into a park. Also
you probably don't need water park tickets. Your resort will have a great pool, and if you are looking to cut costs, this is a reasonable way to do it. Actually, most resorts have at least two pools, even the values.
What will it cost for you to get a room at a moderate? These rooms have queen sized beds, so you'll all sleep more comfortably. The room has 2 sinks, with a curtain between the sink area and the room, so you can make a dressing room of sorts. There's also a fridge and coffeemaker in the room, making in-room breakfasts easier.
Regarding character meals, if you are paying OOP
I'd do breakfast at Crystal Palace and at Chef Mickey's. Breakfast is the cheapest OOP character meal, and if you do it at a later sitting, it can double as lunch (in fact, at the latest breakfast sittings, they bring out the lunch food as lunchtime nears, and you can have some of that, too). With these 2 meals, you get the Pooh Gang and the Fab Five, and can avoid some really long meet&greet lines in the parks. If your DD is dying to meet princesses, maybe you and she can do b'fast at Akershus and let your DH and DS skip the girly stuff, if they aren't into it.
Keep looking, keep thinking, keep crunching the numbers. On our first trip, we stayed offsite, at dinner at our hotel every night (residence inn, so we had a kitchen), didn't do a single TS meal or see a single evening show, and still had a marvelous time! Face it, it's DISNEY!! Don't think about the things you aren't doing; focus on the amazing time you are having!!