Which part of Alberta are you going to reside in? Edmonton? Colder and winters are more snowy. Calgary? Warmer with chinooks and less snow on the ground. Both are not good places for Corvette winters. It can be done, but why? The big wide tires out back on a C5....winter tires don't go that wide and when they do, they cost an arm and a leg.
4WD is not mandatory. It helps but a good set of winter tires and sensible driving is good enough. 4WD just gets you going faster, doesn't help you turn or slow down.
I have driven many cars in the winter. RWD BMW, FWD Honda/Acura, RWD Mercedes, AWD Acura. With patience and a bit of level headed behaviour, the snowy winters are not that difficult to navigate.
As for your Vette, leave it over there. If you bring it over and decide it's not for you, the difficulty of selling a RHD Vette is going to require a substantial hit in selling price. 38K gets you a good M Roadster 2000 or 2001, an RX7, a Supra TT...so many good cars in the used market for that much money. Get a feel for the quality of the roadways before deciding on a car. Some of the potholes on some Alberta roads have been known to swallow small children and Yaris hatchbacks.
Welcome to Canada and the board.