WWHHHOOOOOO!!!! I LOVE this thread. I want to be a charter member of the club.
Being rather cheap, no, make that frugal, we've never stayed onsite. The first year we went, 1992, they didn't have the Value Resorts, so we opted for Holiday Inn Main Gate East. (Still remember Holiday Hound.) Heck, we didn't think could afford Florida, period, at the time.
If we were a party of five, we'd have to get two rooms, and with itty-bitty kids, we wanted to be together. Don't know how we discovered the condos and villas, but we were hooked. With five of us (a couple of years we were eight) those onsite rooms just wouldn't work. Now, we wouldn't dream of the Value, or Moderate or the Luxury. The DVC properties would be perfect, but nobody is willing to give up a kidney just yet. We're August people and even renting points, it's just too much.
About five years ago, my DSIL was determined we'd stay onsite at least once, so she called and asked about the accommodations. She asked what the rooms were like, to which she was given the answer "2 beds, a door, and a bathroom." She hasn't mentioned onsite again.
People talk about the transportation system. I take a bus every day to get to and from work. THIS IS VACATION. I DON'T WANT TO STAND ON A BUS. Granted, my brother whom we now call Christopher Columbus, has taken a wrong turn now and again, but we're flexible. You find some of the most interesting places when you get lost.
We have no problem renting cars. We have freedom. We travel all over the place. (Kennedy, Orlando proper, Sea World, Universal (every year), Busch Gardens, not to mention the Disney discount stores. We feel like natives. And the resorts.... Celebrity, Celebration, Westgate, the Palms, Lindfields, Calypso Cay and places I don't even remember any more.
All I can say is, there is nothing better than getting back from the parks, pulling a couple of cold brewskis out of our FREE refrigerator, sitting on a screened porch, and taking in a Kissimmee or Orlando evening while the clothes are washing or drying IN OUR UNIT.
I love Disney World, but being a grizzled old city dweller, I have to have some contact with something like reality that I get from being able to REALLY enjoy all that the area has to offer.
As for the Magic.... I'm immersed in it when when we pass through that wonderful arch welcoming us to Disney World.