@MarquisDeSade has made posts about his experiences with homelessness, and I have dipped my toes into the life myself.
The first thing you need to know is that what applies in normalfag society is just as true if not moreso if you're homeless. Namely, to live comfortably as a homeless person requires good manipulation or people skills (think getting people to give you stuff, especially food, and being aware of your surroundings).
The silver lining to this fact is that there's nothing like a trial with homelessness to NTmaxx, and make you more aware of social dynamics. But it is an unforgiving environment where you are liable to be preyed upon by thieves and even homosexuals (the term "bum" originates from hobo culture for a reason).
As a homeless person, you generally want to stay away from other homeless people, and ensure that where you sleep and such is private.
You are more likely to find such a setting in an affluent neighborhood than a poor one with various hobo jungles. But you must triangulate distance from other homeless people with having access to resources, which is where things get complicated. Homeless people congregate where they do for a reason, and you will tend to gravitate towards the same areas.
