I was playing with the calculator from See Ya Real Soon and it's pretty interesting. I'm not sure which way I would go to be honest. It pretty much comes out a wash for me based on what kinds of things I put in.
It'll be tricky for me to decide because when we go it will be the first time since 2000 for both me and my husband. And I've never actually eaten anywhere at WDW besides a few random CS places and snack kiosks. So we'll have no opinion on any place, and there's a lot we'd like to try.
We drink a lot of pop and like to get desserts. Apps we only get sometimes but some on the menus sound really yummy. Some I'd rather have instead of an entree. I don't know what kind of character meals we'd do, but I'm sure there would be at least one or two.
It's a way down the road but strangely enough this is fun for me.
That spreadsheet IS really awesome! Maybe they'll let me post the link?
http://seeyareelsoon.wix.com/seeyareelsoon#!dining-plan-calculator/cxc0
I downloaded it a few weeks ago, and it's definitely accurate, as it got me within a few dollars of my own calculations. It would definitely save some time for anyone who knows basically where they're going to eat, but doesn't know exactly what they'll eat when they get there or doesn't want to take the time to look at every menu.
DH LOVES the dining plan. He's an eater, and he's all about the convenience of it. However, it doesn't make sense for us, especially since DH pretty much needs 3 full meals a day. This leads us to purchasing extra meals that aren't included, unless we go with the Deluxe plan, which makes even less sense.
According to my calculations for our upcoming trip in April, the Regular Dining Plan would cost us around $350 more than paying out-of-pocket. I agree that if it looked as if it was going to be around $100 or so, I would probably give in to DH, but $350 is too much to ignore.
The Quick Service Dining plan would be about $200 more (if it still included 2 snacks a day, I suppose it could be a contender, but we like several TS meals)
For $350 less, we can get sodas, snacks, and desserts sometimes. The reality is that we'll probably order water and split desserts. I also don't see us all getting a snack every day, since we'll have 3 full meals, but I do have a few budgeted in for each of us.
We can split or skip meals altogether if it suits us.
I also have added to our OOP budget, some additional food for our 2 year old. While he'll easily eat his fill at the two buffet-type places we're eating, we may need to order him a little extra at the al a carte places and at counter service places. There's also the possibility that he might not eat, when we sit down for meals (he's usually pretty good about it but the excitement could overwhelm him) and it will be easier to just buy him something later, instead of trying to take something away and figure out a way to store it safely.
Another inclusion is resort mug that come with the dining plans. I don't really understand them, but we're not big soda or coffee drinkers. If we were on the dining plan, we wouldn't need them at all, because our soda needs would be covered by the drinks that were already included.
We decided to get the mugs on our last trip, because we figured it would be easy to get our money's worth, since we weren't on the dining plan. We did, but just barely. In general, I found the meal that we ate at our resort tended to be breakfast, and since they don't have juice or milk in the soda fountain machines, it was basically a wash. We did use them for hot chocolate a few times, and for some soda during other meals, but we likely would have spent around the same amount of money without them, and we wouldn't have had to deal with the mugs in the parks after they were useless.
It's entirely possible that the tables will turn next year, as DS will be 3, and we'll have to start paying for him at buffets, so my dining plan calculation years are definitely not over. I expect I'll have to test both options for every trip to Disney we take in the future.
There's definitely not a straight forward answer as everyone is different.