Just finished a 13ish day trip (Aug 25-Sep 7) which included 2 days in Charleson and 10 days of Orlando plus travel, and for a family of 6 (who sometimes fed extras), we spent $1300 for the week total. And we ate what we wanted, when we wanted in our offsite condo. I also spent large on groceries ($370, which included food, alcohol, and condo needs and I did 1 main trip and a smaller follow up later in the week on a rainy day) and let my family lead the way on food. If I'd have done character meals at the Disney hotels, with 4 Dis adults and 2 kids (and sometimes 5 with my mom), I'd have probably spent that amount in 3 meals...here's how we did it...
2 fast food lunches on drive down (before Charleston and before Orlando) $60
Homewood Suites breakfasts/dinners in Charleston Free
BBQ Lunch and Water Ice in Charleston $60
Dinner at Sis's House Friday Night Free
Groceries in Orlando $370 (included 12 pack of beer, a cheap bourbon 750, and a huge Kalhua mudslide bottle - handled our alcohol needs well all week, except for some Chocolate Emporium and Deep Blu splurges - also splurged on beautiful lunch meat - proscuitto, thick cut bacon, pepper turkey - and rolls and gorgeous fresh fruit)
3 days of BOGO 1/2 price Universal Counter Service Meal Deals (4 adults/2 kids) $280 (used 3rd day's worth over our 3 1/2 days there) - hit Springfield and Harry Potter restaurants for main meals - the Springfield Fish and Chips (or Basket of Bait) and the Chicken Platters are awesome, as are the HP ribs and ice cream
Outta Control Magic and Dinner Show at Wonderworks $96 (Groupon Deal) + $12 Tip = $108
Chocolate Emporium for 2 - Dinner and Drinks = $60ish dollars (tax/tip included)
Deep Blu (2 Magical Dining Month Meals and Shared Wine Pairing) = $86 + tax/tip = $115
Disney Springs Gelato = $16 (rewards money)
Hash Hash a Go Go = $43 for 7 (tip included) - Travelzoo deal
Cowgirls Rockbar = $44 for 6 (tip included) - Posted same day 1/2 price deal onsite
Pat O Briens = $36 (tax/tip included) for 7 + $40 from old movie/meal tickets = $76
Sweet Tomatoes (twice - family favorite) = $50 x 2 = $100 for 7 (tip included - had a birthday coupon and other coupons - we split as 2 groups to use 2 coupons each trip)
Wa Wa Hoagies = Free (I fed my brother's kids lunch with groceries we needed to use up and drinks for the adults and he bought the grown ups subs and pretzels)
Resort sundaes/ice cream sodas for 9 = $24
Auto Train (dinner and breakfast included) = free for meals
A few extra butter beers = $20
Total $1376
Total Paid Meals Out = 12 meals, 6 snacks (10 meals for 6/7 people, 2 date night meals for 2 people, 6 snacks for 6 - 3 in CS plan and 3 paid separately)
Total Included Meals Out = 7 meals (3 meals at hotel for 6, 2 meals on train for 6, 2 meals done by my brother and sister for 6 - we had food/plans for these, but we don't turn down family
)
So, we averaged an "out" meals about 1 1/2 times a day and the groceries paid for the rest of our meals. And my kids didn't want to go out anymore than we did.
And for 6 (4 Disney adults/2 kids and sometimes 7 with my mom), we did it on about $100/day just finding regular deals available everywhere and never saying "no".