I read the book Sidewalk a couple of months ago and it was saying how some panhandlers if they go in the right spot and know what to do can make over 70 bucks in a day or so.
I have seen statistics that are a lot higher than this for Toronto but maybe they were made up?
My problem with giving money to homeless people is that it is immediately burned away, usually not on food. I work downtown and I see the same totally crazy looking homeless people day after day grumbling and sleeping on the subway and generally being stinky useless members of society. I'm not angry at them or anything, but if you argue that they are anything but useless dregs then you are dumb! I'm not a libertarian and believe that homeless people should be cared for by the society as a whole, but I just don't see the point in given them change. I am pretty cheap though!
I'm not trying to come off as a dick here but I just legitimately don't see the point in it. If someone could explain to me the end result of giving these people change I would be most obliged. Don't say "SO THEY CAN EAT YOU DICKHEAD" because there are a huge number of social systems set up to ensure they aren't dying that they aren't taking advantage of. The fact that they have a brain problem that makes them unable to accept help from giant organizations designed to give them help isn't going to be solved by me throwing some pennies at them.
edit: it is important to note that Toronto has a disproportionately high number of crazy street people to regular homeless people who need the money to survive, and they are everywhere stinkin' up the city and it has made me incredibly callous toward them. Sorry I am an asshole!
Also it is important to note that most people playing instruments, especially if you see them in the same place every day, aren't homeless people they're buskers. They have to get a license to play in that spot and pay taxes and shit. These people do this as a job and giving them money is cool (unless the suck then they should be encouraged to go away and let better street musicians play).