Re. Canadian theater: I defer to Emma, but from everything I've heard, Toronto is the NYC of Canada, at least as far as theater goes.
Unfortunately there isn't a lot of crossover between Canadian and American theater. I'm not sure exactly why, but I think that, on the one hand, Canada has a lot of pretty sensible culture laws that exist so they don't get totally swamped with US (read: Hollywood) imports. On the US side, it was to do with the fact that we're totally disinterested in other countries, with the exception of theater buffs having inexplicable hard-ons for big English plays (I like UK theater just fine, but I really don't think it's particularly better than anywhere else). The Drowsy Chaperone was a big commercial hit in Toronto that went straight to Broadway, but I think it's the first of its kind. I actively seek out international theater in translation or otherwise, but playwrights who I'm pretty sure are huge in Canada (Judith Thompson, Brad Fraser, Daniel MacIvor) are pretty much unknown here.
As a side-note, Emma, it's awesome that your parents are actor/playwrights. It gives me hope!
