Well, I chose my home mountain without ever having skied it. I figured if I could ski Camelback in PA for 27 years, anything would keep me happy. I had been looking for a retirement destination for a while as we'd always said we didn't want to retire to NJ (where we were living at the time). So, I convinced my husband that the best way to find a small town that was open to newcomers and had some "culture" was to find a ski town. He wanted New England, I wanted Rockies. I convinced him that New England was bone-chillingly damp and not for oldsters most of the year and that the Rockies had a drier cold. He didn't like Colorado ("too brown"). So, started looking at Canadian Rockies, New Mexico, PNW, Sierra Nevadas, etc. for a ski area "no one" had ever heard of. Why? So the real estate would be cheaper, of course. Made a short list of areas and started looking at real estate prices. Winnowed out some more. Started hitting these areas at Easter vacations and found Whitefish. Loved the place we stayed (BIG FACTOR as they were so friendly and welcoming), loved the townspeople (in Safeway they bagged our groceries and asked us if we needed help taking them to the car!!! Incredible to someone brought up in the NYC/Philly metro areas.) Found lots of fantastic restaurants that didn't leave us with totally empty wallets, a local brewery, two handy lakes, Glacier National Park (also relatively unheard of by many), an airport where large planes landed only 15 minutes from the town (and you could find parking and everyone in the terminal was super friendly and there were only three gates and it was squeaky clean). Anyway, snagged a real estate agent or two and drove around a lot. Decided where the best deal was for acreage (ski area is only 16 minutes away and at the time it was $15k an acre...now $85k an acre...). Bought some land that August exactly where we wanted it. The theory was it was our "retirement" home. BUT, daughter wanted to move NOW, even though she was still in school. And we felt silly visiting our empty land each year. Finally skied there after we owned the land, turned out to be fantastic ski area. Then 9/11 happened, a mere 35 miles from us. The papers ran obituaries for months and months and months. Looked at the idea of moving while my daughter was still in school. Decided it was going to happen in between her sophomore and junior year or it wasn't going to ever feel like her true home. Decided that if we were lucky in our real estate sales and built our house in stages that we could JUST do it that fast.
So, here we are, five years later. The daughter was able to race for the mountain while she was in high school which helped her make friends. The house is ALMOST finished. We get by financially, although we do worry about my husband losing his job. (He telecommutes and makes WAY MORE than the normal Whitefish person.) As long as he stays employed, it'll be a successful move for us. If he loses his job to someone in India and has to look here it might be really tough for us, however.