The difference I see between the homelessness BlueLava is talking about versus what xxanxx is talking about is that the latter is more or less PLANNED. People who choose to live on the road out of a sense of adventure rather than desperation typically plan it out fairly well, I'd bet. Before they get their security depost back and give their boss the finger, I think most have given some very realistic thought to where they're going to sleep, how they'll find food / gas / drugs, what they'll do about staying somewhat clean and respectable when they need to, and most of all, how they'll make enough money to get by.
There are, and have always been, hobos, or people who have life on the move down to a science and wouldn't have it any other way. In some cultures there are even whole classes of people who've been on the road for centuries! (Britain's "Pikeys" come to mind.) I'd venture a guess most are not only very street smart, but also very good networkers, who know "somebody" vitrually everywhere they go, both settled people and fellow hobos.
It seems to me certain social skills would take on especial importance to someone PLANNING ON living homeless:
*** Never forgetting a name, face, or conversation, even if it was only one encounter long ago.
*** Leaving no trace as a guest, never "making onesself at home" too much.
*** Being able to spot someone who'll likely buy a sob story or offer something of help, as xxanxx mentioned.
*** An arsenal of quick and confident replies to the question "ExCUSE me, what are you doing there?"
*** Always keeping something on hand that anyone would appreciate as a gift.
Becoming homeless out of desperation, like most things done out of desperation, is a whole other kettle of fish. BlueLava, you're talking about people who don't even have the chops to make it in ordinary society, let alone at the mercy of the elements.
chrissie, I'd say begging and panhandling are both pretty depraved, and should ONLY be done out of real desperation, when all other options have been exhausted. It makes me sick when I hear stories of some hot girl who'll dress in dirty scanty clothing on a streetcorner, collect hundreds of dollars in a day, then go back to her b/f's house and order pizza and a MovieOnDemand. How can some people be so shameless? If pimps harrass her / try to get her on board, good. She deserves it.
As for travelers who lie / steal / con their way across the country / world? All I can say is karma travels faster than the fastest airplane, and WILL catch up to you someday. And you, too, will deserve it when it comes. If you don't have it in you to live on the road honestly and show the proper thanks to those who've helped you, you shouldn't try to live on the road, because it's people like you who give vagrants a bad name.