When I was a kid, my family lived in Florida close to Disney and we didn't have much money. We went to Disney when we could (man, I could NOT sleep on the nights before those trips!) and we'd economize on *everything.* It was tickets then, and we'd just pick up other people's discarded tickets or ride the free rides over and over and over, and we always brought our own food and drinks. As a kid I just knew that buying stuff in the park was for other people.
Now, I have enough money to afford a proper Disney vacation. Not often, mind you, but we could do it. And we were going to...but the fact is, even though I *can* afford it, I just don't enjoy spending, for example, $4 on a bottle of water. Maybe it's my upbringing, but it almost physically pains me. So we stay offsite so that we can have a kitchen and make sandwiches, and pack lots of food when we go.
We had planned to do a vacation where we stay onsite for once and get the dining plan and all, but when I saw how much it would cost.....again, we *could* afford it, but, it just doesn't seem reasonable! So we'll do our little trips here and there with our offsite place, unless I catch a really, really, really good deal. I'm not sure I'll ever feel comfortable paying an outrageous price for something like a pretzel. At least with a watch or a car there's resale value...