Sorry to hear this Fairy, while I've never been homeless, I did experience sleeping on a bench in a bus station while cold outside so I can adjacently related...kinda..sorta.. you know....sorry to hear.
I don't know where you live, but I do make a habit of talking to homeless people, randomly, just to hear what they have to say, nothing more nor bigger in meaning. And while most of them wish they would get out of their predicament (truly want it), they (in almost the same amount of cases) have an addiction of some sort, usually drinking. At least that's how it is where I live.
Regarding the thread's topic, If strangers come at me with passive or peaceful intentions I have no qualms with talking with them. I never give out money, if someone needs food or water, I'd buy it for them but not money, I want to make sure my hard earned cash ends up exactly where it should.
If someone is being aggressive though, that's a different matter. It really depends if I'm alone or not, I tend to be more aggressive alone and away from home since my wife can't become a collateral victim in a fight or its aftermath. While I say that, I haven't been aggressive in years, I mean over 7. Before I was married, anyone who would yell at me or be aggressive I'd just stright out knock em out. Wouldn't risk me getting hurt because someone else wanted to start a fight. I never did start one thus my hands are clean in that way.
Little story:
A few weeks ago I went to get my 3rd anti-COVID Shot (#TeamPfizer). There's been something that kept annoying me for the last year, a lot of people started biking (cause you know, covid and its implications). There is a law in my country: bicycles are mandated to function only on special lanes meant for them, if those do not exist, they must stay on the street. Sidewalks are not allowed to be used by cyclists, unless there is a special designated bike lane.
Goood, I was walking with my wife towards the vaccination center and OF COURSE, a bicycle rider went by me. He was pissed I didn't move from his way so he could pass since he rang. Now.... I'm a fairly well built guy. Good height, good muscles, good size. I'm not scrawny, so.... yea.... hit me..... I dare you. He didn't , he slid past, I told him that it's illegal to be on the sidewalk (in a calm manner) and then he stopped about 50 meters in front, took off his helmet, gloves off and started stretching. He was sooooo ready to fight. My wife was startled and told me that when he passed I should not have told him that, but I'm a cool guy and I wanted to get my shot not fight so I keep walking forward, when I get close to him, the guy starts going off "DA FUQ MAAAN, U THINK U COOL ? CAUSE YOU WITH THE LADY? WHY WONT YOU MOVE". In the most calm manner, I look him in the eyes and tell him "Because there is a law, and I don't feel comfortable when you break it and expect me to bend to your will." Of course he says there is no law, I started reciting the law, he said it doesnt exist, I pull out my phone, show him and he just mumbles and leaves.
Lesson in life: When a confrontation is coming, look them in the eyes and speak SOFTLY, like you would to a baby going to sleep. It fucks up with the human brain, they expect a fight and instead of a physical one, it becomes a mental one. Even if you lose it, it will hurt less :D
TL;DR Strangers are fun, you learn stuff from them. Except aggressive ones, those just need to be ignored.