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I know this thread has been made several times, but I think it's always good to update it for people who might be getting the itch. I myself as someone who is relatively new (a few years anyway) to the "bumming" game would love to hear other people's thoughts on relocating to live out their skibum dreams. I'll just kick out some of the obvious ones for now.
I think saving up some money is really, really important. Sure, you could probably throw your shit in the car and drive off with just enough gas and beer money to get where your going, but only if you have your plan 100% dialed in ahead of time. It's cool to sleep under the stars in Hood River in July, it's less cool to do it in November in Jackson.
Obviously amount is pretty variable depending on everything from the cost of a pass (sled, A/T setup....heli?) to cost of living in the area, to how you get where you're going. As a general rule of thumb, I'd recommend saaay......3 months rent and food (gas if you'll be driving/sledding a bunch). That's a guess off of the top of my head, but the idea I'm trying to get across is that you probably need MORE than you think you do, so keep that in mind. In the financial department, I'd just also say that if it's at all possible find a job before making the move and/or do your research as there's nothing worse than showing up in a seasonal/tourist town in an off month when NO ONE is hiring with no money in your checking account. If you don't have a checking account, you're too young to be reading this suggestion and if you're presently considering making a move involving skiing and becoming a pro or something, stop.
I tend to see embarking on a ski migration as a private, solo act, but a lot of people pull a TJ and drag their less talented friend along and later get them avalanched upon. Obviously moving with a friend/lady has its advantages and is sort of a built in security blanket, but it also can go horribly wrong and/or hold you back from having the experience you're looking for. In other words, consider what sort of person you're potential roomie actually is, and more importantly what sort you are.
For a lot of people bringing someone along isn't in the cards by choice or not, but there's a ton (more) options for someone flying solo. Craigslist, local papers/classifieds, coffee shop bulletin boards, etc. are all good places to find roommates and/or rooms. Hell, call a realtor from the area and feel them out on what's available and what properties are going for and if there are better months to find places/get better prices, all that stuff, etc.
Going along with the research up front theme, REALLY figure out what you want to get accomplished. What I mean is this:
Are you moving to SKI? Or, are you moving to be able to ski more at a better resort whilst living your life outside of skiing/progressing towards some larger non-skiing related goal?
This might seem stupid to point out, but honestly this is one of those questions that will really shape your whole bum experience. It also may seem like I have a preconceived notion about which of those two types of "bums" above is the "right" one, and I really don't. The truth is that they're both great reasons to relocate; they're just really different animals. For those though that are really considering moving to basically live, eat, and sleep skiing I HIGHLY recommend STILL researching the area you're moving to HEAVILY as far as things you can do outside of skiing. Injuries happen, other things happen...it's good to be somewhere where you sort of have a plan b, or at least some other reasons/things to enjoy being there. For example, I really love live music, sporting events, museums/art, etc. so I live fairly close to a city that offers that. All I'm saying is don't move to a shack in the middle of nowhere to shralp pow only to blow a knee if you're the sort of person who likes to catch a late movie and eat greasy pizza at 2am.
That's all for now, I have to go to work (one of the many, many reason why ski "bumming" is sort of a misnomer for most of us).