I live in Cabbagetown, and I know a lot of homeless and street people, but mostly by sight recognition, not by name. I never ask people on the street what their name is, but I introduce myself, if they do first.
I sometimes give money to people who are begging, usually if I know them, or if they're sitting quietly with a sign; never to the 'pro', who asks for a handout.
Lesson one of panhandling school: get 'the Mark' to say "Yes" to some question. In Montreal, this was usually "Do you speak English?" In Toronto, it's usually "Can I ask you a question?", or similar.
I collect beer cans and liquor bottles for a guy who's homeless, and spends most of his day collecting beer cans and liquor bottles. As far as I'm concerned, he's a working man with a lot of competition. Anything I find, I put in a bin on my porch, and he collects them 2 or 3 times a week. I could use that money, (average about $20 a week in summer, maybe $10 this time of year), but I don't need it. He does.
I'm also "Ghetto Santa" in the 'hood. People in Cabbagetown often leave things in front of their homes that have value to somebody. When I see something that I consider valuable, like a knapsack, or a coat, or an abandoned bicycle, I'll often pick it up, and give it away to someone specifically, within five minutes. I usually leave abandoned bikes at the corner of Sherbourne and Dundas East, and walk away. Someone will take it within a couple of minutes; I don't care who it is. They will notice who left the bike. I never try to sell something that I find, or that's given to me for free, except precious metals. I'll sell found silver or gold items to a pawnshop.
I get free bottles of water often, and I usually give them to street people with a dog.
I make regular donations to a fund to build an Islamic school for girls, in the donation box at a local Muslim-run grocery store. The people there are very friendly, and I know that 100% of the donation will go to the cause. I never give money in grocery stores or Shopper's Drug Mart when they ask, because I know that the store owner can claim 17 cents of tax credit for themself from every dollar that a customer contributes.
There are a lot of scam charities, where the majority of funds received goes to staff salaries and perks, and a small percentage goes to those to whom the charity is geared. The Salvation Army traditionally has the highest percentage of funds donated going to the needy; a bit over 80%. In many cases, that percentage is ten or less.
I can walk through a really rough neighbourhood at 3 AM, without concern for my safety. I don't owe anybody any money, I haven't fucked anybody over, and I mind my own business, Plus I'm six foot two, with a large frame. Street punks don't start beefs with someone my size for no reason, and I don't give them one. I know street etiquette. Actions speak louder than words, but what speaks louder than actions is what other people say about you, when you're not around.