Portland, Oregon. Lots of shuttle services to the mountain. Mt. Hood.
Bend, Oregon. Lots of shuttle services to the mountain. Mt. Bachelor.
Ashland, Oregon. Lots of shuttle services to the mountain. Mt. Ashland.
Personally, I'd pick Portland. Daily bus service to stops in the coast range (fantastic mountain bike trails) and Oregon coast. Too many retired Californians in Bend and Ashland. Property prices are outrageous in all three as compared to income. There was an article in the paper this morning comparing housing prices and home ownership between Iowa and Oregon. Housing costs three times as much in Oregon with about the same average income. Of course, there's a reason for that. People like living here. Even when its raining.