Toronto, Canada. 1) salaries are low compared to the US. 2) on a per capita basis, we don't seem to start/host great startups (lots of lame knockoffs of US ones, but, targeting Canada). 3) Public transit is terrible. 4) if you live outside of downtown and work downtown, you may lose two hours a day commuting. 5) compared to NYC, London, Paris or Berlin the cultural institutions seem not commensurate with our population (the largest art gallery, the AGO, has a grown man's toy boat collection in it!). 6) if you bike in the city you are almost killed on a monthly basis.