Sounds pretty Beat. I'm curious, was it more interesting as it happened, or in retrospect?
Very beat, and Beat. Heavily influenced by the Beats as a youngster, and even moreso by "You Can't Win", by Jack Black (no not the bag of contemporary hot air, the proto-beat hobohemian of the early 20th century...a must read for all) and so lept in....I had done a few cross country hitchhiking trips on zero dollars, so an extended stay wasn't too far of a leap. It was incredible at the time, and probably a little rose tinted in retrospect, but undoubtedly still amazing. You throw yourself into the wind with nothing, and you want for naught. My intro to living the Snyder/Kerouac boddhisatva way...
The hobo culture was alive and well, and still is. People really do cook beans over fires in the southwest and swap tales of railroad bulls and yards to avoid. Great way to see the country. If you are young and exude a trustworthy air, people even take you in, feed you, give you work....
I had also recently kicked dope for the first time, so I was especially zealous, and liberated. And I took it all in, had my backpack, would do some labor ready shit when needed, hit up food banks, dumpster dive, shoplift as a last resort. My ideals were very strong then, however misguided, and my stamina great. See the rose tint?
Seeing the country from a speeding boxcar and sleeping out under the stars can't be beat. You want for nothing, and have only the moment to be concerned with. 90's zen in full effect....the Clinton years were full of excess, so there were plenty of droppings from the table to feed on.
I can honestly say that period was probably the happiest in my life.
Other trips I went with more resources, and some even with automobiles and flush, but the poverty of freedom of the aforementioned really highlight as the best.
Passports are not a hassle at all. Quite simple really. Get the gumption some day. And if your unmet financial obligations are student loans, well, I never paid mine. Well, not exactly true...after I found the way to convert lead to gold (um, not alchemy but chemistry, and that is an analogy) I paid them off. And went back. And dropped out. And went back. And dropped out. And never paid those off... So far so good. And it's been a long time. I also never paid my taxes during the Bush administration, but the vast majority of my income was unreported. I owe them a bit, they send threatening letters every now and then, but I move around the country constantly so who knows...I have sent a few threatening nonsensical letters back, just taking the piss for my own amusement...