Actual place names should not get translated, ie Trois-Rivières for example should not be translated to Three-Rivers, even though that is indeed the meaning of the name. Montreal could get 2 categories, since the English spelling without the accent is easily understood by all, but tehcnically, it is called Montréal. With the accent.
As far as regional categories go, after confederation is simple, the provinces as they were added had a name and stuck to it. Prior to that, indeed things get wild, particularly with the Canada-East/West Lower/Uppper-Canada, which were actually used concurrently in everyday usage. In school, I do recall that there was Upper and Lower Canada, but Canada-East/West never got mentioned at all, so may have been strictly a governmental paperpusher sort of thing. :D I can help you out for this part of the country if you want.