Holy shit... Didn't expect so many replies.. haha
First of all, Thuxen, that is fucking AWESOME. I used to do that around the US, never stayed in a single city for more than 2-3 months, then I would move on to a new place, and constantly rotate where I was.
I've grown up a little now, and I think doing the same thing on a fucking worldwide scale would be EPIC.
Moving on... Thanks for all the tips and suggestions guys... This is a good topic, because I'm sure I'm not the only son of a bitch that would love to get away from this place.
As for what my priorities are, I'm really not sure... That whole backpacking Europe idea is excellent, but it is something I could see myself doing for a few years rather than just a few months.
I haven't traveled outside of North America (US, Mexico, Canada), and this summer will be my first time in Europe. A friend of mine is stationed there, and is flying me out for the last 3 weeks he is there. Me and him grew up together, lead the same type of lives (minus the whole US Guberment job idea), and he said he abso-fuckin-lutely loves it there, and doesn't want to come back.
That should be a good experience to start with...