This is the first time we have gone without the dining plan (we have always had it free and once we paid for deluxe dining) in 8 or 9 trips. It's killing me trying to make a budget. A) I am not a number crunching kind of gal enough to sit and pour through the menus, B) no matter what I estimate it seems like not enough and too much at the same time

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Currently our room, tickets, and travel are paid for. That is for 2 adults, a 16 yr old and a 9 year old.
All that is left is food and spending money. We aren't huge spenders. The kids usually have around $100 each (partly their own money and partly what we give them). We have a car rental booked for $200 for 9 nights.
That leaves food and tips and some groceries for the room. We have 8 table service booked and the rest are counter service. I thought maybe $220 a day for food would suffice. Most of our table service are the less pricey ones (lunch at Sci Fi, The Plaza, Via Napoli etc).
So I am looking at bringing about $2500 to cover food, tips, rental car, and misc. spending for 9 nights.