We can classify chronically homeless people into two distinct categories: Passives and Predators.
The Passives usually occupy about 80 percent of the transient landscape, the Predators about 20 percent.
The good news about the Passives is exactly that; most of them don't want to be contacted ("hassled") or arrested by the police because it interrupts their ability to do nothing significant all day.
We can define Passive homeless (the 80 percenters) as those who simply wish to wander around, get a little high, eat, use a clean bathroom, beg for money from time to time, and hang out with their other Passive pals. They are not usually confrontational, unless they are really drunk, high on drugs or their mental illness worsens, and they do not usually follow, harass, threaten, or harm people who choose not to give them spare change.
We can define Predators (the 20 percenters) as those transients who prey upon whomever they can find, either aggressively, criminally, sexually, or violently. They steal from normal people; they steal from other homeless people (no honor among street sleepers, so to speak). If you see a male transient wearing either a handsome men's blue blazer or an attractive woman's coat with pink fur on the collar, he either picked it up cheap at the Salvation Army thrift store or, more likely, he stole it from the back seat of a car after breaking the back window.
Whether Passive or Predator, their favorite haunts are the public library, in or around large city or county buildings, the parks, the beach, and the downtown areas of your city. You might find them in the woods Camping with other transients.
Being homeless can be tiring work. Imagine this daily schedule: walk around all day in too-hot and too-cold weather in clothes that aren't right for either condition; try to keep other transients from stealing your stuff; move in and out of various stages of sobriety (wake up in the park with a blazing afternoon hangover); try to keep yourself fed; perform the never-ending search for a bathroom; and stay away from the cops. As such, the Passives usually hit the bedroll and call it a night around 2100 to 2200 hours. These folks are down for the count until daybreak, huddled in the alcove of the closed store, inside the back-alley apartment laundry room, or bundled up on a bus or park bench. (And while they may be asleep, they are still often holding something sharp and defensive in one or both hands.)
The Predators, however, like to come out at about 2200 and get into the business of their evening. They are either chronically homeless (because they have stolen from their friends and families) or sporadically homeless, bouncing from menial jobs, to jail, to the streets, to weeklong drug and alcohol binges in bad motels, back to jail, and so on.
They are choosing this mean life. The Predator homeless avoid the outreach that could get them off the streets. Unlike the Passives, who may be stuck in a rut of substance abuse, mental illness, bad luck, and bad choices, the Predators like roaming the streets, hurting people, and mixing it up with you.
This choice makes them erratic, violent (just because it's fun for them), and much more likely to escalate to more serious crimes, like purse snatchings, street robberies, sexual assaults, and engaging in beat-downs upon people they come across as they roam.
Keep your head down and keep the faith,