Pro for Toronto- only 4.5 hours by car to Beachwood
Con for Montreal 9.5 hours to Cleveland...
But the main info that was missing:
Toronto: Cheap rent (considering) avg $1200 for a two bedroom
Insanely high prices to buy. A starter home in Thornhill is $450k and down south it's more like $650k, and that's in might expensive loonies (and toonies).