Absolutely, you *could* play for money. Plenty of people tour overseas and get paid for it. But, you'd need to do the legal legwork to find out what is involved, and it would be a good idea for you to line up your gigs *before* you got stateside. In many areas, you could busk without going through all the hassle of having to get a permit, or having to go through the hassle of contacting pubs/events/venues or legal permission to work in a Country with which you are not familiar.

I imagine some of this hinges on how good you are as well. If you could send a demo tape or the like to an agent in the US, and let *him* handle the legalities and logistical crap, that might save you some headaches, but I suppose that would depend on how much the rep thinks he could get for getting you gigs and publicising you. If the answer is that it would be questionable, then likely as not, the answer would be "sorry, all booked up with clients right now".

Good luck with the journey...it sounds like an interesting trip, if you can make it happen.