I saw a flag like the above in a window of Essex Hall at the university where I am employed. It's not that surprising - there are many Italian-Canadians in the city where I live. 

I like the flag, actually. Our Italian Canadian presence has been underrated since the days of John Cabot. 

I'm not afraid of those who consider themselves "hyphenated Canadians". That being said, I think the attempt to continually hold the Canadian experience to a non-Canadian ideal that is somewhat misguided.

Case in point. The owners of a house on Campbell Avenue have painted the two rocks that designate the beginning of their driveway with the tricolours of the Italian flag. To me, this is perfect encapsulation of this metaphor: you can paint the over the Canadian wilderness with another nation's colours but it can look really stupid.