A lot of homeless people have jobs. Jobs are in the city. Are you suggesting all the homeless need to do is rent a parking space downtown for their Bentley and they can commute from a nice tent in a farmer's field outside of town?

For goodness sakes, a shack on a lake north of Toronto goes for millions of dollars these days [0].

A few years ago a conservative government in Alberta tried to solve their homeless problem by giving free one-way tickets to Vancouver to the homeless instead of welfare cheques. Dumping your problem on someone else converts a cost into an economic externality but is sure to get you hated.

[0] http://muskokacottagesforsale.net/real-estate-properties/