You might encounter some squeegie kids at busy intersections - mostly punk teenagers and 20-somethings who carry a squeegie and wait for the traffic lights to turn red so they can wipe your windshield for spare change. Though turning on your windshield wipers usually deters them, it's best to have some coins handy just in case, because I've heard about squeegie kids punching windshields and cracking them if the driver refused to pay.
You'll often see them downtown or in the Plateau Mont-Royal, not so much in posh or residential districts (I've never seen any in Westmount or Outremont).
Watch out for an older woman in downtown Montreal (close to McGill) with two crutches and what appears to be a leg-related disability. She's maybe around 50, long dirty blonde/graying hair. She will appear to be having trouble with her crutches (one of which has a missing screw) and will ask that you please help her across the street.
She's very sweet, with big blue eyes but beware! She will say that she's stranded as her ride fell through, she can't take public transit and she can't afford a taxi (where you come in). She will also probably tell you that someone told her to "take a plane" when she asked for a ride.
I gave her money the first time I saw her, thinking she was a poor woman really in need, she came up a month or two after with the EXACT same story, looking for money from my husband, she's a scammer.
You'll be asked for money along the street pretty often, sometimes in rather elaborate ways. Put your game face on when you pass and say the magic word: "Desolé." For you non-French speakers, it's the equivalent of "sorry" and the pronounciation is something like "de(h)-zo-LAY". You could try to sound apologetic like you really mean it, but regardless, once that word leaves your lips it'll be quite clear to the other party that they should leave you alone. In fact, if you overdo the apologetic tone, they might get offended!
I've been to Montreal now on several occasions and the problem with street folk here is much the same as any other city.
I do have to agree that experiences with panhandlers and I have been a bit interesting/scarry. They dont get physical towards you but the way that they ask for change or money seems to be quite agressive. It may come on strong but if you simply keep walking or acknowledge them by telling them "sorry, no change" or whatever then they let it be.
Its not highly uncommon to see alot of homeless/street people in and around the Berri UQAM Metro Station and the park beside it, i have to say on many occasions you'll see homeless people sleeping on the benches and sidewalks in this area...dont let it phase you, they arnt going to do anything.
Every large city is going to have homeless people and beggers, but we found most of them to be very aggressive in Montreal. Being two girls out at night it was a fairly scary experience to have a man follow us down the street yelling at us because we wouldn't give him money. That being said however, the street was always crowded so we never felt in danger for our lives, but it definitely was not a good experience. During the day we never had a problem, but in the evenings some of them seemed to get bolder.
As youll see, Montreal has a lot of beggers and what we call Squeegies...Squeegies are actually punks and Skinheads who wash your car's windows at red lights for change! Youll see alot of them around town especially in the eastern french part of downtown between Old Montreal (Rene-Levesque) & Sherbrooke, St-Hubert and St-Laurent blvd. They are not dangerous. Just tell them that you dont have change or put your wipers on, if you dont want them to wash your windshield! :)
There's a lot of beggers in some areas. Most of them won't bother you much, I've never seen a begger actually attack someone, and never heard of such stories. I enjoy having conversations with them whenever I have some free time.
Despite the government's efforts to house and feed everyone, you will still find more than a few bums in montreal, especially downtown, who prey on naive tourists. Many will come up to you and ask "Do you speak English?" Just keep walking, it'll save you a spiel! Most beggars in Montreal will only spend the money at SAQ (liquor store) anyway.