Our family has been twice, and other than some aspect of trip (such as food, or transpo) paid by in-laws and we did have a wonderful multi-family experience. It is true that other than a cruise trip when I was in HS, I never went on vacations like that when I was a kid, but I wouldn't rule out doing another one, even if we were paying. This winter I priced out similarly high level of included activities resorty vacations such as: cruise, inclusive resort to Yucatan, Key West resort, and they all priced out the same or higher than staying on site at Disney at a budget or moderate resort. So I think Disney execs have their finger in knowing what the pricing is for similar "experience" vacations and they are still "competitive" in that sense especially as flights are cheap and don't require a passport for American visitors. There are also many websites that show how to stretch your dollar at Disney so that also reduces the hurt.
That said the best deal we had was driving to the Smokies and staying in a cabin and doing Dollywood, Splash Park, and a day or so in Gaitlinburg, surrounding area. We had 8 family members and it was very enjoyable and relaxing, really nice accomodations, incredible sunset views, and less expensive than Disneyworld. So most likely we will do either that or Williamsburg for the next "nice" vacation (every 2 or 3 years).
