What a fantastic thread. I'm so glad it got bumped up for me to see it.
I think this was a great idea for fun or for real budgeting on its own, as the OP intended it, but it also made me realize that with the way our family eats we could totally make this work by sharing meals and staying with the fact that we are real water drinkers.
Things to keep in mind about us: Most likely, next time we go we'll be a party of four, me, DH, DD11 and DD13 So that is 40/day times 4 people for 160 dollars a day in my plan. I don't like for the kids to eat a lot of sugar and empty calories and get less healthy and more cranky while on vacation. So as lovely as all that sweet stuff is, I'd rather have healthy happy kids who can enjoy their vacation and not get sick while on it. Which means we are prone to skip all the breads, and cupcakes and pastries that fill up a lot of people's food pics and trip reports. I really like to get to go into a sit down restaurant at least once a day and more is nice too. As a general rule, neither of my girls wants a child's menu or any version of a "kid's meal" while mom and dad are getting to try good foods. My DD11 sometimes eats like a bird and then portions of her food end up in other people's stomachs or in the trash. My DH actually does this at times too. And any of us might do it if we are just too hot. OH and I have a gluten problem but I just left that out so that I could play this game with more fun and less complication.

In truth I have no idea how the gluten things plays out at Disney while you are paying out of pocket. So my imagination just filled in here that I'd skip bites of certain things and they'd make me lovely gluten free versions of other things for the same price.
So... knowing that the meal sharing, water drinking, grazing and appetizers could work beautifully for us, I set out to see if I could make a plan for our family for DHS where my family could get to go back to Mama Melrose's and I could try some other places AND where I could just skip traditional breakfast fare as well as sweet breakfast rolls and such. I'd rather start with an early lunch or savory snack.
And these two days are what I came up with:
DHS day 1:
Starring Rolls--
2 Turkey Foccaccia sandwich with chips or fresh fruit 9.19x2x1.065
=$19.57
Brown Derby--
2 Sweet Corn Chowders - with applewood-smoked bacon and ancho chili oil $8.00x2
Brie, Midnight Moon and Prosciutto Cake with Tete de Moine Petals, and an olive-roasted vegetable salad $11.00
Cremini Mushroom Chévre Tortelloni-$9.00
Blue Lump Crab Cake--$12.00
16+9+11+12x1.065x1.18
=60.32
Starring Rolls--
2 more sandwiches with chips and or fruit (either ham or turkey this time)
=19.57
Sci-Fi--
Mixed Greens $7.49
BLT Soup $6.99
7 bean beef chili $6.99
Butcher Steak $22.99
7.49+6.99+6.99+22.99x1.065x1.18
=55.87
1st DHS day's total= 155.33
in truth as big as those sandwiches look we'd probably end up skipping the mid afternoon extra sandwiches which would make our total =135.76 for the day, but then again if we did we might also make up the difference by adding on at SciFi. lol. We are somewhat sporadic.
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DHS day two:
Min and Bill's Dockside Diner--
Franfurter in a Pretzel roll $7.59
Chicken Caesar Sandwich $8.09
7.59+8.09x1.065
=16.70
Toluka Turkey Legs--
2 Turkey Legs $7.59x2x1.065
= 16.17
Catalina Eddie's--
Pepperoni Pizza with Caesar Salad $8.69
Hot Italian Deli Sandwich-- with Caesar Salad $8.69
Caesar Salad with Chicken $7.79
8.69+8.69+7.79x1.065
=26.81
Mama Melrose's
Crispy Calamari for Two $12.99
Chicken Campanelle $18.99
Pork Osso Buco $21.99
2No Sugar Added Mascarpone Pound Cakes - with linoncello-macerated berries and fresh whipped cream $6.49x2
12.99+18.99+21.99+6.49+6.49x1.065x1.18
=84.14
DHS Day 2=143.82
On this one I'm left with lots of wiggle room where I could add on an extra item somewhere.