20yrs ago Hamilton was pretty great. Then Mel Lastman started busing out the dregs of Toronto to Hamilton, which started a two decade orchestrated gentrification of downtown Toronto, until even the homeless can't afford to live there anymore.
But in the last 2-3yrs Hamilton has turned around, 3000 exchange students (and their Asian parental unit funding), expanding art scene (hey mafaqu'er, Hamilton has hipsters too!), and the Hamilton music scene would always kick TO's in the balls, and laugh.
Oh and since we're talking about home ownership, Hamilton has led Ontario three years running on rising prices. Throw in great public transportation options (40mins from Hamilton to Union Station, in rush hour, you can't even do that from Georgetown, let alone Woodbridge).
There's a reason downtown Hamilton right now is the best real estate investment in the GTA.