I can see where you're coming from, but it's slightly different. I never just go on the road to make a trip from here to there and then I'm done. When I'm on the road, I live there. Usually for months or years at a time. Starting out with money is one thing, but it dries up quick. Usually I try to keep away from the stuff all together. Free food abounds (even if it came from a dumpster), especially in the states. Water is free, and shelter (as our society knows it) is overrated. Assume makes an ass out of you and me. I never expect other people to pay my way. If I fly a sign, it usually says something funny or something simple like "Be happy." Also I usually am trading for the cash by way of providing musical entertainment, some spinning of the ole practice poi, telling jokes, or whatever.
Also, I usually am on the rainbow trail working for free food kitchens, where we have nothing and turn it into food for hundreds of people who otherwise didn't have any. It all balances out, it's a circle. And it's not as black and white as you seem to think.
Once again, money is an idea. There is no federal reserve anymore. Your greenbacks aren't backed by gold sitting in a trust. National debt is in the billions, man. So even if someone does want to "pay my way" as you so high-handedly put it, they're doing so of their own free will, with currency that's only REALLY worth as much as the paper it's printed on and the abstract idea of value that we associate with it when it suits our purposes. I'll burn a mountain of dollar bills and laugh about it because it doesn't matter. It isn't sustainable, and the grocery store might as well be a crack addiction.
If you really wanna get into it, why don't you try building your own house and growing your own food for a while. Because if that isn't what you're doing now than you, sir, are not paying your own way.
Thanks for the comment.