This sounds like an interesting plan. I'm in the south east U.S, any suggestions on where to apply? What state would be the best? I've got $1k laying around, for a single dude I can make that stretch.
Vail (Colorado) is big enough to need an IT department and have a night life. Denver is a fun city but I agree with original reply that you should get into the mountains.
Mammoth Mountain. It's the best in the USA. Plus you would be gaining residency months in California, which has the best community college system in the USA. You can go to CC in CA for $20 a credit and then transfer into Berkeley if you take the right classes and get good grades.
Smuggs is fun (prefer Stowe and Okemo, tho) and I love Vermont but the economy there (and anywhere in NE besides Boston) has been in the dumps for years. You'll have to move out of state once the season is over. Plus, all the Northeast resorts are full of grouchy telemarkers and finance dingleberries from Boston and NYC. Mammoth Mountain is filled with olympic snowboarding hopefuls during the week and hot chicks from LA on the weekends. Also consider Big Bear if you want to maximize the social aspect, but it's a much worse hill.
The downside is that it's hard to actually get a job at Mammoth because all the spots are already taken by Australians. Also, the available jobs that are easy to get are usually in food service.
I did Park City, Utah. Best snow on Earth and
SLC is 35 mins away and has a burgeoning startup scene (even their own YC style program in BoomStartup). Rent is about in the 500 - 600 range. Less if you live 20 south in Heber.
Park City is in my mind way better than Mammoth and SLC is a short hop away. Utah isn't exactly California but it has Boulder and Denver near by if you want to run to a "heavy" startup scene in the summer.
I was burned out of a job 2 years out of college and decided to drop it all and head to Jackson Wyoming. You are locked off from a lot of civilization but you meet some amazing people, have plenty of time to ski/snowboard and code. Needless to say I have been away for 2 years and miss it dearly.
Big props for the east coasters. Sunday River (home town mountain) in Maine if you want is amazing as well. Hop a train, you are in Boston in 2-2 1/2 hours.
