I am planning on first, finding a Skyline for sale in Japan less than about 15k hopefully. Then, shipping it to Canada, i'll get a plane ticket up there then drive it back through the Canadian/US border (since Canada and the US can trade freely(North American Free Trade Act)). Then i'll get it legalized some time in that year which only costs about 26k. Below 40k for a Skyline is not bad at all. I was looking for a GTS or GT-T R34, any year, in good shape, and can at least make it home with from Canada. I'm going to really mod it too, i'll get a new engine and transmission and switch it to AWD and stroke it to a 3.0 (or 3.2, i can't remember what that kit strokes it to) and after that I don't know the specifics of what I am going to do. Anyone think the importing thing would work though?

No, there not legal in Canada.

I don't think it will work.
how will the car be driven legally in Canada?
which country's registration will you use when crossing the border?