I confess that I have traditionally been a "medium" steak eater, but am slowly coming around to medium rare.
Anyway, here is the best steakhouse in Toronto (and as such, the best I've been to, although I have been to a couple high-end places in Montreal). I've been to every high-end steakhouse in the city, and this place is le shit.
http://www.jacobssteakhouse.com/They dry-age the steaks on site, and the menu changes daily. They don't just offer you the choice of cuts, no, they even offer you to choose between the different farms their steaks came from.