I was born and raised in Calgary (actually, a third-generation Calgarian, beat that :P) and I love it here. 4x4 put it brilliantly ... there are problems with every city, and Ken, I think you hit the nail on the head, that a lot of people doing the complaining (not your friend, Dion) are those who didn't get in on the housing boom and aren't so much bitter about the city as they are about missing out.
My whole family is here and that is of the utmost importance for me. I could live anywhere as long as they were there, and almost all of my friends are here as well. I don't see myself moving anywhere else ... even if I won the lottery, I'd probably just pay off my mortgage and buy a condo for the winter down south