There are essentially two non-exclusive strategies: you can get along okay by raiding dumpsters, foraging and hunting in nature and generally being as independent as possible, or you can freeload from other people. In the latter case you’ll need to become as social and gregarious as you can. It helps if you’re hitchhiking or street performing then you’ll automatically meet people and help and connections will come your way.
Stay as clean and presentable as you can. If you dress like a down and out hippy or bum then you’ll be treated as such. Your unruly beard and face piercings may win you kudos down at the beach but if it stops you getting lifts when you start hitchhiking around then you’d best shoplift a Gillette razor.
If you’re a guy life will generally be easier if you shave regularly and both sexes should take care to stay clean. No hobo is so poor that he can’t afford a bar of soap. You can wash at least your arm pits in public toilets or else you can wash your whole body in the park with a bottle of water – stand in your underwear so as not to offend anyone too much. Brush your hair and keep your nails short, too.
If you plan to busk or street perform then it’s even more important that you make an effort with your appearance. If you want to make money then you have to look like you’re worth money. It’s amazing how few people understand this on the road. You don’t have to put on a tie but don’t wear dirty clothes with holes in. Go for something extravagant.
Get to grips with the local language as soon as you can. You’ll soon learn the words for ‘are you hungry’ but to maximize your opportunities you’ll want to soak up as much vocab as you can and fast. A pocket bilingual dictionary is an excellent investment.
You can reduce your traveling kit to a basic survival pack of: a sleeping bag (or blanket), a water bottle, a knife (for cutting bread and cheese etc), a piece of string (for a clothes line), one change of clothes, and a bar of soap. No harm’s done by carrying a bit of ginger and garlic with you as medicine either.