Join Date: Dec 2006
Location: Laguna Hills California
Bikes: Cannondale R3000, Specialized Enduro SL
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What I would do if I was in your shoes is pick a place you think you would enjoy living during the winter and find a job there, use it as an oppurtunity to tryout a town you were always interested in living. See if you can save up about 300 dollars and go on Craigslist and find someone renting out a room on a month to month basis. Give them the first months rent, then save up for your next tour while working and living in the area...
If you have trouble finding a job, go to a temp agency or a day laborer place.
Another idea, since you have some bike shop experience I believe is to find a busy shop and ask if they hire bike builders. If you can put together pre assembled bikes pretty fast you can make up to 15 bucks an hour, then go do dishes at a resturaunt in the evening.
Work your butt off for a few weeks in one place, find a good stealth camping spot and continue on until you run low on money again or until you land some side work.
See if you can use your connections from your last tours sponsor, and network a job from that.
Good luck and have fun.