Six of one, a half-dozen of the other...
Well, Phil, you've gotten some good suggestions. I know nothing about many of them and a little about a few of them.
I've always liked Steamboat. It's far enough from a major city like Denver so that it has to have its own services like several automobile dealerships and a decent hospital. A number of chain retail operations that you are accustomed to and may like having are also present, so you don't have to pay ridiculous prices for, say, groceries. The ski area is generally very good, with very good snow (usually), although the relationship between the town and American Skiing has not always been good. In any case, it's been purchased by a branch of Intrawest, so things will change - for better or for worse is difficult to predict. Steamboat also has a nice climate in the summertime (6,700 ft), along with several golf courses, a river through town, a lake about 25 mi north of town, and great backcountry for both skiing and backpacking. It has numerous summer festivals and cultural events. Real estate tends to be fairly expensive.
Colorado Springs is too far from skiing, IMHO, and notoriously conservative. Maybe that's OK, maybe not.
If two hours to Winter Park is OK, you might consider Fort Collins or Windsor, CO. Both are developing rapidly. Windsor is a bedroom community for Fort Collins/Loveland. Numerous golf courses are available, and Fort Collins can offer employment to both counselors and Subaru salesmen. The climate is usually quite mild (this year excepted). Fort Collins is a university town. I lived in and around there for over 20 years.
If you have to work in or near Denver, Golden might be more convenient than Evergreen, and it still provides good access to I-70 and skiing.
Sandpoint, Idaho is close to Schweitzer and is very
pretty, with plenty of golf and water. I've seen real estate ads for places north of Sandpoint that look pretty reasonable, but I've never checked them out in person. I don't know what the employment situation is like there, either.
British Columbia...As you can see from the upper-right-hand corner of this post, I've managed to make the move to Canada, so I know a little about it.
First, whether it is hard or easy for you to move across the border to live depends on a number of things. A work visa for me was easy. I'm an engineer and it literally took me less than two hours to secure a job offer in Nelson. There is a shortage of technical people in the BC interior. Nelson, like Steamboat, requires some services locally because there are no large cities within a couple of hours. The work visa could be difficult or impossible for other professions, at least around here.
I am now a permanent resident. I obtained that fairly quickly (compared to how long it takes a Canadian to achieve a similar status in the US) because my wife is a Canadian citizen. I could have also obtained permanent residency based on professional credentials, but it would have taken longer. The paperwork requirement is substantial no matter how you do it.
Second, be aware that the medical care system is not a reason to come here. True, it's much cheaper than it is in the US, but let's just say you get what you pay for. Even though Nelson is the same size as Steamboat, the available medical facilities are much more limited.
Someone also mentioned that six months of cloud cover can get depressing. 'Nuff said.
Given all that, Fernie is certainly worthy of consideration. It looks a lot like Colorado and it gets more sun than Nelson. Still, I'd probably choose Steamboat over Fernie if I had to make that choice.
Rossland is also worth a look, although, like Nelson, it suffers from fog and clouds in the winter. Also, the ski area is at low enough elevation so that it rains there entirely too often.
On the other hand, real estate in Rossland is surprisingly reasonable, and it's dirt cheap less than 10 miles down the road in Trail. Of course, the Cominco smelter in Trail doesn't exactly improve the ambiance of the place!
Rossland and Nelson look different than Fernie, too. The wetter weather has created dense, green forests. They're gorgeous, although various people are trying to cut them down as fast as possible. There are numerous large lakes in the area, generally long and narrow with a north-south orientation. The main body of Kootenay Lake is some 60 miles long.
Nelson's local ski area is small, with only two old, slow double chair lifts. The snow is awesome, however, and there is some amazing terrain accessible with a little traversing. The base is higher and the microclimate slightly different than Red Mountain, so it gets a lot more snow and a lot less rain.
The BC interior is cat ski and heliski central, if it matters to you.