I looked and coulnd't find any stats on Canada's homeless isssue. not even on the government page Statistics Canada, mostly because they can't agree to a definition of homelessness.
On the East coast there isn't too much of an issue. I think it's because of their lower cost of housing. Also there is a smaller gap between the poor and rich, the "middle class" remains strong, unlike places such as Toronto. The East coast per capita makes the least ammount of money in Canada, however they give the most to charity. I think is because of a genuine empathy to people in a hard place financially and they try not to let their fellow peeps fall through the cracks.
Toronto and Montreal have serious problems with homelessness with the white collar folks litterally walking over and on people sleeping on the streets in the business sector. in Toronto the homeless seem to be quite looked down upon however accepted/tollerated.
Winnipeg has a large problem with homelessness especially with Natives but i haven't spent much time there to know much first hand.
In Vancouver and Victoria it's at an epidemic status. Victoria is the warmest place for canadian winters so a lot of people (youth) migrate there. There are homeless people everywhere...everywhere downtown. but they are really nice people and dont seem to "bother" any locals and tourits. they come up with clever signs and are quite friendly. i've had great times with transiant and local streeet folk there. i've also seen one of the nicest smiles i've ever seen in my life on the streets there. Victoria takes care of it's homeless there, they have lots of facilities and resources. On the other hand we have Vancouver with it's grimey seedy underbelly and it's rampant drug abuse(smack,meth,and booze). I know people there who are afraid to walk in entire blocks of the downtown because of these problems amongst occasional violence. Vancouver is hosting the 2010 olympics and this problem will have to come to the forfront. right now the government is trying to sweep it under the rug by opening methadone clinics(safe injection sites) in places further mainland in B.C such as Vernon.
All i know for a fact is that Canadian homelessness is on the rise