If you're serious, then you will do what you can to find contract work. Contract work may very well require you to commit to crappy work schedules for a couple of months on end, but the flip side is that when the contract ends you are free to do as you please (like take 3 months off to go snowboard).
I do not think that the current climate is ideal for giving up a decent salaried position, but if you are willing to sacrifice a big chunk (maybe all) of your savings, then you could try it.
There are people who survive off of very little income, but keep in mind that doing so means that you
1. Probably won't be able to have a lot of possessions/stuff (unless someone stores them for you)
2. Will have to learn to accept less-than ideal living conditions (crappy roommates or tiny living arrangements with little or no privacy, etc).
It would probably be a better idea to find either part time work in a location close to a hill, or a job that lets you move your hours around.
On my last trip to Jackson I met a guy in his early 20's who had just moved there and taken a job as a programmer. His boss was cool with him coming it at ~ 12 or 1 as long as he got his hours in and his work done.
a 25-30 hour a week job will still let you get more than enough riding done, IMO.
Read on another forum: "If someone held a gun to my head and said, "You have to move to Salida tomorrow", I'd probably do it. If they told me I had to go to Breckenridge instead, I think I'd just let them pull the trigger."