In respect of the issue of certain homeless folks being a problem on the system in one fashion or another; I would support using an integrated team, for a limited period, (8 weeks?) that goes to all the known trouble spots and responds to requests for intervention. Such a team should include a mental health support work, a shelter worker, a social worker, a police officer and an empowered representative of TTC.
The object is not to simply oust people who have nowhere to go, but to provide them a viable alternative, with an involuntary assist in leaving the property an absolute last resort.
Clearly there are people out there who need intervention, some may accept that but not know where to turn; others may wrongly believe they're fine.
Whatever the case, action is needed but it ought to be restrained and as respectful as possible in the circumstances.
Better to give someone a good reason to move on, and help in doing so, than to use any kind of force.