Although you can enable Cortana in Canada now using the Region trick, location based support is still spars. I think their plan makes sense; once they have the proper data support available so that the experience is useful, it'll make sense to make it available.
Bing search seems spotty at best here. For example, Cortanas restaurant recommendations are abysmal. Her dinner ideas for me are the CN Tower and Piri Grill House, 4 miles away... I live in downtown Toronto. She also seems to have issues with time to leave alerts that aren't "home" or "work", even though they're added to my favourite places, and she has serious issues finding addresses in the city when doing an address based search. She often gives results in other cities...
They need to get Bings data up to snuff, or Cortana will be a joke when they launch it in Canada. Hopefully that Microsoft-Foursquare deal back in February will dramatically improve Bing and Cortanas database for locations.