Damn that is a tough fucking question...Off the top of my head though right now...
Large Sum - Would have to bury myself deep in interior BC with a truck, sled and cabin from November till March. Then I would head north to Alaska and blow whatever I have left on Helicopters and rent out another cabin for the inevitable down days that would consume most of the months of March and April.
I could go crazy trying to pick a single place to spend a season, especially when you throw in a decent amount of spending money. I think Europe would be high in consideration as well, not because of the terrain or snow - but because of the lifestyle you could live for a season. I'd go for France, Switzerland, Italy, Austria and Germany.
Damn this question sucks.