Hey there MTN,
Sounds like we have a lot in common. I'll try to answer your questions the best I can. We've only been in Pagosa since May, so keep that in mind when reading my opinions. I also realize you may know some of these answers I've provided since you've visited many times.
We strongly considered moving back to Teton Valley after Montana, but the biggest reasons against that were the housing was getting extremely limited/expensive and yes, the wind! (So, I know what you mean about that). It is breezy here in Pagosa, but part of that is due to where we live 20 miles south of town in a bit of a wind tunnel between the mountains and open meadows. Still, it's not nearly as bad as TV. We also found TV to be a bit too conservative with the LDS influence.. not a huge deal, but it was obvious with several things, especially after we left. That would not have kept us from moving back, however if the wind and housing issues were not such a concern.
Weather... As you're probably aware, drought is always a concern anywhere in the west. However, I think Pagosa is a bit more susceptible to it than TV. We are on the edge of the San Juan Basin here... which is more or less the beginning of the expansive desert southwest.( There have always been water concerns in this area, and you have to be careful if you buy property with or without a well). Most of the time, we rely on storms that only come from the south or southwest... most other directions produce little precipitation. (Teton Valley can bring in storms from the SW and NW.)
As far as reliable rafting, I don't know if that's something you can always count on here either, but the San Juan's ( and Wolf Creek) seem to do a pretty good job at pulling in the snow... however, I think it is still more volatile than Targhee/the Tetons. (TonyC confirmed that with his snowfall stats for both ski areas). You will get more sun here for sure... nearly 300 days, vs TV's 200. That is a big reason we left Montana as Whitefish got only around 150! We didn't think Teton Valley was that bad, but that's somewhat relative for people. Both valley areas average around 20" of water a year, and roughly 100" of snow. Overall, it's warmer here in PS, but nights always get pretty cool thanks to the very dry air.
Yes, Foghee can get a bit annoying at times, but after living in Whitefish... it seemed MUCH less of a issue! I think Wolf Creek is a place where if it's cloudy, it's usually snowing...otherwise, it's often sunny. While I've only been to Wolf Creek once (last year during a dry spell).... I think Targhee blows away Wolf Creek for terrain quality/variety. But it's known to have quite a few epic powder days, and low skier density, so there is that. Wolf Creek also submitted an expansion plan last year to add a couple more lifts and terrain, so if approved... a few years from now, it could be a bit different place with more variable terrain.
The TOWN...
Pagosa's year round population is officially only around 1700.. but that's pretty misleading. The county population is upwards of 15,000... with the majority of that being within 25 miles of Pagosa. While I still feel it retains a small town vibe, it's been very busy/touristy this summer so far. (Much more so than TV was/is)... locals say it's the busiest they've ever seen. Even so, other than traffic on US 160 that runs through town, I haven't felt too overwhelmed by it. Part of that is that we live 20 miles south of town on 35 acres, but even when going to town... you can still get in and out of the stores, etc without wanting to strangle people. There is often a wait for to eat in the early evenings at many local eating places, but we've gone before or after the "rush" and not had any problems at most spots. Spring was not busy at all, and people say winter is pretty mellow here, except for the holidays and some weekends. Even when busy, it just doesn't seem all that "touristy" to me, like a Jackson or anything... but definitely moreso than TV as there is a lot more to do here than in Driggs or Victor other than get a bite to eat to/from Jackson/Yellowstone/Targhee.
I know what you mean about the CO attitude (I have lived and vacationed in Summit Co), but I've not experienced that in Pagosa at all. People are very friendly and accepting so far, and we've made friends a lot easier than in TV or many other places we've lived. There are tons of community oriented events here, and many more options than TV, IMO. It's a bit bigger community, so you might not have quite the intimacy of TV with some of those things. Same goes with amenities... many more good places to eat and shop (including 3 excellent brewpubs with great food). And while some things are closed on Sunday, it's nothing like TV. There is also Walmart that opened up a couple years ago in "uptown", which normally would be a turnoff to me in a small town, but it's a small-ish Walmart, and very nicely done... and sits back off the highway with structural mountain theme design.
The hospital in town is expanding and seems pretty well equipped. I've had some bad experiences with the primary care dept, but they are mostly billing and communication issues, not the care itself. Probably the biggest issue we've seen is getting help with our house remodeling. People in that industry here are horribly unreliable/flakey. Of course, we didn't have good experiences in TV with people in that industry either, so it's likely somewhat of a small town thing. I haven't noticed that issue with any of the other services in town, however.
My wife travels quite a bit, and she has flown out of DGO a couple times. It's about 60 min to the airport, and it's small, but effective. Winter could be a bit challenging driving during any storms, but not anything worse than going over Teton Pass to Jackson. DGO is expensive though, as you might expect... maybe even more so than JAC. My wife just chose to drive to Boulder, CO for a conference instead of fly because the rate to DEN for an hour flight was $650! Part of that is the season, and part of it is United being greedy assholes. It's a bit cheaper to fly to SLC and a few other locations. Great Lakes Air also flies out of Alamosa (2 hr drive) that is quite a bit cheaper, I think.
Pagosa is pretty isolated by most peoples standards, maybe just as much as Driggs... but Pagosa has more amenities, so it's not as noticeable to me as it was in Driggs. Durango is about 60-75 min from Pagosa proper, where you an find quite a bit more shopping/dining and a few of the big box stores (Home Depot, Super Walmart, etc).. Farmington NM is about 2 hrs away (not been there yet), and has ALL the box stores and a Sam's Club. Albuquerque NM is about 3.5 hrs and has everything. That's where we go for our quarterly Costco runs (it's only about 3 hrs from our house). CO Springs is about 4:15 and Denver about 5.5 hrs.
We also considered McCall, but it seemed even more isolated to me, (with limited amenities for being that far from anything else). The avg sunny days there are actually similar to Driggs (200 days/yr).
Overall, Pagosa has been on our list for some time... after TV, and Montana. There is no perfect place out there with everything we all want, but after renting for 5 yrs in all those other places, we finally decided to settle down here for a while based upon visits, and tons of research and comparison charts :-D . You better hurry though if you want to buy, as prices are going up here... still below many "resort town" areas though.
Feel free to PM with with more questions!
Todd