www.hitchtheworld - that kid is my hero.
While in Mexico, I met a girl who had been traveling north for 2 years, selling beautiful jewelry that she made to get by. Do you play any instruments, can you make anything to sell, etc. etc? Also, there are TONS of ways to get free accomodations; check out things like WWOOF, helpx.net (they have quite a few volunteering opportunities down there); sometimes even (slightly) paid positions are available. There are lots of ways to make it work, you just gotta do your research and make yourself available. Of course, nothing beats actually BEING down there, b/c you can meet shitloads more people that way...
As far as my own personal experience - hitchhiking is easy as heellll down there, and the Mexicans are really very kind and open people (I believe it's in part due to the fact that they have more first-hand experience with true poverty than we do in the States; as such, they are infinitely more giving). Didn't really hitch much in C.A., as I was only in Guat for a week or so... Food is incredibly cheap down there. I was spending around $100/week, and that was WITH hostels, restaurantes, tourist attractions, buses, etc. - wasn't really trying to save money that much... It can be done infinitely cheaper than that, though!
Pending on whether I get this shitty-ass job that I'm interviewing for tomorrow (and manage to not go crazy with the mundanity, and keep it for 6 months or so), I'm **tentatively** planning on flying down to Lima, Peru next fall (you can get flights for $250 from Ft. Lauderdale through Spirit Airlines), then doing stints of volunteer work through helpx from there north until whenever... Of course, this is all subject to massive change, but I'm definitely gonna be lookin' for partner
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Aren't you on some sort of probation or something? That shit sucks ballllzzzz...