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With respect someone who stayed homeless for that long must either have done so due to personal preference, drug abuse or disability.
There is a significant difference between an itinerant laborer and a homeless person.
You can work for accommodation and food, the accommodation could be a farmer allowing you to sleep in a barn or set up a tent as this costs them nothing.
Itinerant workers often carry tools if only for show, tell everyone they are passing through on the way to somewhere else and are looking for work.
Lumber yards, brick yards, cement pouring yards- these places have little that can be stolen, the workers are tough to begin with and they may find the prospect of overnight security appealing.
You may find work at night as a concierge in a small hotel/ whore house, you will actually earn decent pay, use the hotels laundry facilities and sleep during the day which is a great deal safer.
Nobody ever wakes up someone in uniform, it's universally assumed that you're just overworked and "I work nights" is a legitimate excuse for falling sleep anywhere.
Many people take jobs that involve travel and so will get accommodation vouchers. Truck drivers, stewards, marine work, primary industry work, cattle, even traveling salesmen.
I would look at jobs that already force people to stay away from home before a non traditional income like pan handling.
Many people do some kind of performing art, huge variety. My favorite are musicians who carry a mouth acordian because these are inexpensive and lightweight.
You get a regular spot that's a respectful distance from a cafe, the trick is playing somewhere people are likely to loiter to begin with, to make eye contact, and get the right balance between being quiet and being close. Ambiance is the key word.
A sticker that says "I love x" (Being the city you are in) will keep you from being moved on.
So rather than sleeping in the woods, just find somewhere it's socially acceptable to sleep and assume the identity of someone nobody would bother.
It wouldn't be stupid to get a McDonald's uniform and change into it to sleep.
People are far less likely to move on, wake up or assault you if you don't look homeless.
This goes even if you're pan handling and dirty yourself for that purpose.
In terms of hygiene, keep your hair short.
It may seem cold when you've got no hat but far warmer when you do.
Use lye ash from burned paper to ward off foot rot, wrap rags around your feet in the Russian manner then wear socks over the rags to keep them together.
If you can't keep the rags washed; better than stink out your shoes.
Wash rags by soaking them in a plastic bag, wrapping one around your knee and rubbing a second against it.
If you can't find water, ask someone to fill up a clear plastic bottle for you, take water from a toilet cistern (not the bowl) or from a fountain or automatic sprinkler system.
Dental hygiene actually isn't so hard, tooth brushes are cheap, inner tree bark or soft wood works just fine, salt water is a universal antiseptic.
You can bathe without water, using either a wet cloth, a rag, sock etc.
Pinch your foreskin when you pee, urine is sterile and it's entirely appropriate to use it on injuries to your feet, ideally though you would use salt water.
Take minor cuts and scrapes seriously and recognize infection is an emergency because it won't get better by itself.
You will have more time than you know what to do with, rather than pace around aimlessly looking for quarters, keep yourself clean.
If you're homeless, make it your mission not to be homeless.
You want to make the world a better place? Do it after.
Don't make being homeless part of who you are, don't accept homelessness.
I've been homeless several times but only briefly and that's why, I stayed clean, didn't take drugs, identified as a worker, got a job, shared accommodation with other workers and came back.