Some good info. In regards to homelessness. Have you even considered that its not a city failure...some people DO NOT want to change their lifestyle and choose homelessness over what is perceived as normalicy. These are complex issues and require complex solutions..its not as simple as spend more money to give things away.
I couldn't tell you too much specifics of what the employment rate is for the IT field, but I do know that a lot more tech companies and businesses have opened in the past few years so I'm sure there are plenty. Employment over the last year has been the third highest among urban centres in Ontario, so definitely lots to choose from!