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I was living in my van in CB for about a month this summer so I'm familiar with that area. Beautiful! but it's such a small place and so remote, I'm wondering if you can find much bud out there? not sure how the herb scene is in CB. If it's plentiful, that might be the town for me. A job would be harder to find there, and that could be a problem..
As far as summit county I was thinking more Vail area.
I'm going out there to ski bum for awhile, but I'm having a hard time finding the right place for me. I was attracted to Vail because of the slopes, but some say it sucks while others say it's amazing.. but I'm not sure the town of Vail is for me. maybe breck as it seems more laid back.
I was looking into Steamboat for the powder, and I've read that yeah it is on the expensive side but not as high class as vail and aspen and still has that small town feel to it where people actually live rather than just migrate from denver to ski. Also read the herb is easy to find there.