I'm a city boy.
The idea of living in Oakville or Vaughan or any burb for that matter is a prison sentence to me frankly. Faceless banal living, no sidewalks, no streetscapes, have to drive everywhere, no subway, no places to go, no energy, shitty restaurants, dust from never ending subdivision construction, miles and miles of pressure treated fence. No thanks. Don't care how many square feet it is or the lot size. If I ever won the Princess Margaret "Dream Home" (which would be a nightmare for me to live in) I wouldn't even give it a second thought. SELL.
My perfect location would be Palmerston Boulevard in Toronto between College and Bloor West. Little Italy to the south, the Annex to the north. High Park Boulevard is also very cool in my opinion.