FrozinballzGotcha that makes sense. Hard to transition to a less steep mountain haha.
I don't really have a work situation, just going to send it and try to work the mountain or clean the shitters at a local restaurant and just do something different. Colorado interests me and I still want somewhat of a town and a cool area to live for a winter or 3.
My advice would be to try to work nights, wash dishes/wait tables tune skis or something, so that you can ski every day. If you are going to the mountains you want your time to be focused on skiing, not just skiing on weekends. I spent half a decade in Tahoe between college and grad school (thought it would be one year but you know how that goes, haha) and I worked nights and taught skiing part-time to maximize time on the mountain. You only had to give Squaw 25 days a year to get the pass so that is what I did. Usually all you had to do was show up on the hour, usually you wouldn't get a lesson so you could just go ski until the next lineup, then they would let you go early in the afternoon. The part-timers were only there to cover lessons when there were not enough full-timers. If you are doing this you want to ski as much as possible.
For pure skiing I would pick Telluride, but it is supposed to be insanely expensive. I would do as much research as you can to find out just what the living situation would be and how difficult it would be to afford day to day life and rent. Unfortunately those factors need to be a part of your decision. Some ski towns are expensive but have less pricey areas within 15 minutes so the locals are able to get by. I don't know if Telluride is this way or not, but you might want to try to find out.
Are you considering any other places? Or just Colorado. Personally I would rather ski bum in Tahoe than Colorado, although I can see people being scared off by the drought that broke this winter. You might want to check out Bozeman Montana. It is supposed to be a great town, it is a college town, and Bridger Bowl is very close. I'm not an expert on it, but it could be worth doing some research. If I were you I would see just how much you could learn about different places before making your decision. You might want to try the Teton Gravity Research forums. It is a bit of an older crowd over there, but lots of people who will have valuable information for you. Some of them will act like idiots, just like here, but don't let that bother you. Good luck.