There's a lot of info on this site in old threads; the DIY section, what to pack thread, and googling tips and tricks can help to acquire some theoretical knowledge. Nothing beats practical experience though, so once you have enough info to survive on your own you should hit the road, with a "road dawg" or not. It can actually be dangerous for someone with no experience to go looking for a road dog online, because you have no sense of who is good and who is bad to stick with... maybe they have very little experience as well and are lying to gain "punk points" or try to look good to gain your trust... and they teach you "how" to do all these things that you really should learn right the first time, but you don't know
what right is, so you're at their mercy.
That said, my recommendation is to find someone in real life, meet them, get to know them, ask them questions and see what they know, what they're willing to share, and whether they're willing to take responsibility for you, as a newbie, on the road. That's a hard job, being a mentor on the street. But some people take pride in doing such a job well, so I hope that you find at least one such person in your travels.
Keeping an eye out for people online in order to meet up with them is fine in my book -- I'd be a hypocrite to discourage it -- but meeting people and agreeing to travel together before you know much about them is a recipe for a mixed bag of very cool and very unpleasant experiences.
I've got no tips for Indy, except GTFO, 'cause I was there for a few days camping out in some of the more horrific t-storms prayin' to
something so my tent didn't get flooded and I wouldn't be left to get eaten alive by the prolific mosquitos. Me and my 100% deet were ready to put up a fight, haha. Anyway, go west if that's at all your thing; the west coast has less of a steep learning curve for travelling and living on the streets. Lots of friendly people (plus plenty of wingnuts of course) but in general a better experience than I've had on the east coast. (warning: subjective statement, advised to acquire more opinions from others, and firsthand experience, before forming your own!)