I've actually done this, finally ended up settling down halfway across the US, and I couldn't be happier now (FL to CO). First you need a decent vehicle. I'd recommend a small pickup, there's always people on Craigslist looking for truck owners to help them move stuff, so you can use it to make extra money. Also, the bed is great to sleep in with a sleeping bag. 4x4, in case you end up somewhere with snow (mine was 2x4, did NOT like snow). 4 cylinder manual, so you get better gas mileage. Bench seat, more comfortable for sleeping on cold nights or if the bed is full. Also, the small cab volume is easier to keep warm than a sedan. Something that's not gonna constantly break down, but cheap to work on if it does. Best option would be a Ford Ranger, they're durable and easy to work on. Chevy S10 would probably be your second best option, that's what I had. And I recommend waiting until after winter, March/April would be a good time to set out. Starting in the spring helps you acclimate to climate change easier if you're "homeless" long term.