Well in case it is useful to others I will elaborate a bit. We did choose Park City and are under contract on a home there. Like all "resort" areas it does have a slightly "fake" feeling but we thought it was less fake than say the Avon/Edwards (Vail/Beaver Creek) area, which felt like it was nothing but a resort. Park City does have many full time residents. Also many commuters to SLC. Most of the super huge, super ritzy stuff seems to be around Deer Valley and the rest of the area actually feels rather normal. The North Synderville area where we are going to live has homes from $400k to $3+ million. Horse property is relatively cheap and pretty close in by most resort area standards. And Park City has lots of conveniences that we really miss after living in a very rural area for 5 years. We lived in Santa Fe, NM, for 18 years before that and got used to a certain level of services and conveniences and, I dare say, sophistication. And with SLC just 30 minutes down the road you have everything you could want in big city stuff. And Snowbird/Alta/Solitude/Brighton are an hour away, which is how far I have to drive for skiing now. Plus I used to live in SLC and have friends in the area so we have a jump start on our social scene. Most important in the end actually was the fact that SLC has a pretty strong economy and should my telecommuting jobs ever fall apart I have ample employment opportunities in SLC.
Jackson - Thought the town was pretty fake and we were surprised by the lack of sophistication despite the reputation for super wealth in the area. It failed on our sushi metric which divides population by the number of sushi restaurants. Property, especially acreage, was super expensive. We felt that the town had a large transient population - young people there for a few years for the "extreme" experience but have no real intention to stay or any roots int he community. We also found the permanent, not super rich part of the population to be pretty religious which is not a negative in and of itself but the large, loud anti-abortion protest outside our hotel was not very attractive. Skiing is limited to Jackson and Targhee and while that is not bad at all it is less than some places. And the weather can be brutal, especially last winter.
Eastern Idaho - Just too small and rural. Basically the same as we are living now in Pagosa Springs, although Targhee is probably a bit better than Wolf Creek.
Steamboat Springs - wonderful town. Great ski mountain. Had a very cool vibe and seemed to be a real town to a large extent for a resort. Horse property relatively close in was pretty cheap. Negatives were a single ski mountain and its isolation. It is a decent sized town with decent amenities and conveniences but it is quite a ways from anything else and economically there would be no real local opportunities for me. This area was third on our list in the end.
Avon/Edwards/Eagle - we liked the area but it does feel pretty fake. Horse property was way too expensive unless we went all the way out to Eagle. Eagle is a nice little community and we found nice properties there but it is 30-45m to skiing (not counting the parking time which can be a bitch) and the amenities of Edwards/Avon, at least from the properties we could afford . Plus side is that within 90 minutes you do have a lot of skiing. We were concerned that Eagle was just a little too "far from the action" for what we wanted. Plus again the lack of local employment opportunities was an issue. This area was still second on our list in the end.
Telluride - we really like the area. Horse property is expensive unless you get pretty far out on the mesas. But in the end Telluride is a very small town that is very far away from everything. Just too isolated.
Durango - very cool town that we like a lot. Good property prices. But skiing is limited - Purg is fun but not really big mountain skiing. Telluride is a few hours away but it is a loong day trip. And Silverton is fun but not something I would do more than a couple times a season.
We considered but did not visit Bozeman, Sun Valley/Ketchum/Hailey, Tahoe.
So in the end PC seemed to offer the best mix of all the things we think we want. With the continued deterioration of the economy the economic issues became much bigger than they were when I started this thread.