If I had to do it over again, which basically means thinking about what I'd do for the next trip

... I think I would see if we could afford to stay club level and maybe not do the dining plan and just pay out of pocket for dinners.
I think we would have to sit down as a family and say "what are the restaurants we would have to do for this trip". Then I'd go through the menus and calculate what everybody was probably going to order at these restaurants, which would be easy because we are predictable eaters.
Then I would compare the out of pocket cost for these meals versus what I would be paying for the dining plan to see which would be a better deal.
THEN I would have to figure out what kind of a discount Disney was offering, and see whether it was a
Free Dining offer or a % off Room Discount.
Keep in mind that conventional wisdom states that
when pricing out a DELUXE resort package, the
Room discount is a better deal than the
Dining Plan discount. this is because you save a greater mount of money on a higher, deluxe hotel room rate
To wit:
30% off of Deluxe 300 dollars per night is a $90 dollar savings versus
25% off of a Moderate $150 dollars per night is a $37.50 dollar savings.
Since the dining plan is a fixed cost (1 table service, 1 counter 1 snack) you would be saving the same amount no matter what hotel you stayed at.
Since we know to go for the room discount and not the dining plan I then would have to see how much they are charging for the dining plan and factor that into my cost comparison versus paying out of pocket versus the additional cost of club level.
It's a lot of thinking and most of it is running around in my head, which is easier than letting it out my mouth and trying to explain it to someone else.
Suffice it to say that pricing out a Disney vacation is just like buying a car. You have to break down all the components of what they are charging you for, for example with a car, it's base price, accessories package a and b and then the special tires that you wanted. You have to know exactly what you are paying so when they say we can offer you this discount you'll know whether it's a good deal because you have all the components that you are buying priced out.
With Disney it's Hotel, Dining plan, Park tickets and then finally airfare, which you can bet you'd do better shopping for yourself rather than let Disney find you a flight as part of your package. Then you start comparing discounts, i.e. room discount, versus dining plan, versus the benefit/cost of club level and how that will impact the amount you pay for food.
All of this is running around in my head. Then I go to talk to my husband and try to explain it and he has a panic attack over the fact that we are going on vacation and we have to spend money. This is the same man who will run out to Home Depo and buy crap all over again that we have sitting at home on a shelf that he refused to check on before he left the house.
Somewhere, God is laughing at me!
Good luck with your trip planning and better luck with your spouse. This isn't necessarily a "Man" thing, it's a "you go one way and your spouse goes in the opposite direction" sort of a thing!
~MM