Hi Airmunkey, looks like you are pretty friendless, so I will give you some advice, I am from Scotland, and have been to Calgary, twice, great city with really friendly people, and the greatest show on earth, the Stampede.
The little smart copes quite well in most situations, and not too bad in the snow if you get an extra set of wheels and put snow tyres on them, if running on standard tyres in snow it struggles for traction.
As it is a semi manual you can make smooth progress in the snow and there is'nt too many big hills in Calgary or surrounding district, so as long as you are'nt making a trip into the rockies the smart should be ok.
I am not that sure just how harsh the winters get up there as I have only been in the summer but maybe someone else from the area will post and give better advice.
Happy Trails.
Ellis