You might be making things more complicated. At the Blaine/BC border crossing for example, you will be asked the question whether you will import the vehicle. If your friend goes with you and if he is not a Canadian citizen or permanent resident, he must have proper documents to enter Canada. If he is a Canadian citizen or permanent resident, he must be ready to answer the question why he is driving a U.S. licensed vehicle (I assume this car is licensed in the U.S.). Canadian citizens and/or permanent residents cannot drive a U.S. licensed car into Canada. If he does not go with you, you need to have written permission from him saying you are allowed to drive his car. If I were you, I would not do this. Good luck.