Not an easy answer...
Here are the scenarios and choices...
Bringing first time guests with us or large doses of the parks:
Boardwalk Villas; you can't beat the location and over-dose of Disney magic that this resort has. A lot of friends that come with us, that have never been, are completely sucked in.
Relaxation, medium doses of the parks:
Saratoga Springs Resort and Spa; the spa is the best we've ever been to, being near Downtown is fantastic and the resort has a great overall feel.
Complete relaxation, small doses of the parks:
Old Key West; very, very relaxing out of the way. Far and away the best porch/patio of any resort room. The porch is huge and can be enjoyed durning any kind of weather. We really enjoy sitting on the porch during a thunderstorm. A 1 bedroom unit is enormous.
Christmas time or Fall time visit:
Wildermess Lodge Villas. Can't beat it at Christmas or the fall.
Food & Wine Festival:
Back to the Boardwalk. Forget the fact that it is next to the International Gateway, there are usually events at either the Boardwalk or Yacht & Beach.
Golf Trip:
Saratoga Springs. We love being on LBV golf course, one of our favorites.
Last minute trip:
What ever is available, there is no place like home! (DVC member lingo!)
I'm sure we missed a few other occasions and resorts, but no matter where it is it is always a great time.