The issue is homologation. The car has to be upgraded to meet Canadian standards, which in several areas are different from US standards. The major issues are daytime running lights, a more secure keyfob system, and bilingual placards. These things can be done with the assistance of Tesla, but they're not into doing it. I know it's been done on very rare occasions, like a couple whose Roadster was destroyed and Tesla helped them import a replacement, but their attitude is basically that they're too busy to be bothered with it.