I've developed an aversion. Some people genuinely need help, but others, not so much.
In Montreal, I saw a "homeless" guy bumming smokes and money off people, and then show up a few hours later wearing nice clothes, incl. an Ecko leather jacket.
In Toronto, I see repeat offenders with different stories. They always wander around with a new story to tell each week, pointing to a "hospital" tag and needing money for various travel expenses out of the city. One guy gave the entire waiting room at Greyhound Station off Bay a whole speech about how he needs to get back to his family, that his son was in trouble with the police, and he was short 50$ for a train ticket. He asked everyone to please, please, please give him something so he could get back home. One lady offered to purchase the ticket for him, though, and he suddenly threw a fit, became violent, started screaming at people and ran straight out the door exasperated that no one would give him money. Obviously if he were in the kind of situation he claimed to be in, he would've accepted the woman's assistance in purchasing the Via Rail ticket! But we all know that he was full of bollocks.
That said, I did help someone once. He asked for food, for money to buy food at the Starbucks across the street. The Starbucks was closed, and I was alone and concerned that if I denied him his request for food that he'd become violent. He seemed nice enough. I bought him a Subway gift card for 5.65$. I hope he didn't sell it for 3$ or something :pink_frown: I wonder about it sometimes.
In Toronto's bus bay, "homeless" people are everywhere. They invade the Subway there and ask for free food constantly and the workers are harassed. It's a sad state of affairs.
I take pre-emptive measures to try not to be approached. I talk on the phone, I listen to music super loud, I avert eye contact. I play my 3DS or read a book. They usually address crowds rather than individuals, so it's a safe way to go about it.
I feel sad for people I find sleeping outside or on bus chairs, etc. There's one guy in my hometown that lives off the money he collects from alcohol bottle deposits. He has a shopping cart and sleeps outside. It's upsetting. One person can't make a widespread difference; we'll have to wait for some kind of movement to really get the ball rolling for housing, shelters, etc.
Ottawa just shut down a popular aboriginal shelter downtown. Lack of funding, apparently. It's sad.