should be tons of kids in your area right now, ocala should have finished up or be close to it by now. although they may be closer to nola right now. my first piece of advice is to go meet some real travelers instead of mystery internet beings.
i'd suggest not travelling if you want to continue college. if you're dropping out or graduating go ahead after this semester but remember, it's always possible to get stuck very very far away from where you want to be when you're depending entirely on other people's charity and "this train appears to be going that direction", or to catch the travelling itch and not be able to stop. consider mommy and daddy's opinions on your new lifestyle choice and if they will continue to pay for your apartment once you're ready to settle down for a bit.
begging is not essential. learn a skill. i didn't play anything before i went on the road, now i play fiddle, guitar, mandolin, and various percussion instruments. being a cute girl with a cute dog and a decent voice, i can usually bag ~$70 in a couple hours busking the right spot.
lice, scabies, mrsa, staph, crackheads, homebums, alcoholics, junkies, cops, rednecks, preachers, lawyers, judges, snakes, rats, thieves, pimps, johns, oogles, hippies. you may not encounter all of these things, but you will encounter some and be prepared to deal with them accordingly. accordingly, by the way, does not mean calling the cops or going to the hospital, because they may not help you once they find out you're "homeless".
hitchhiking isn't scary, i hitchhike alone frequently. be confident and friendly, say no to rides if you are sketched out, carry a visible knife [i have a machete for "camping"]. however, i've only ever been in one sketchy situation while actually in someone's vehicle, and they were just on meth and driving too crazy. i asked to get out immediately, and he kindly obliged. people tend to be nicer than you think.
not everything you see on tumblr is as cool as a sepia filter makes it look.
as i observed when i really first started out [by myself, i might add- see, not scary!], a portion of travelers are drawn to the lifestyle because, like us, they are bored kids who don't really want to get a job and would like to have an "adventure". there are also some people who do this because they are totally batshit fucking crazy and it is their only choice left. after a period of time, many of the kids from the first group evolve into the second. it's not a pretty sight. don't become one of them.
[i think i just got trolled real hard]
it's a little scary leaving an apartment that mommy and daddy pay for and living nowhere on practically nothing, or at least I imagine. 
