You will definitely get pulled over as I did when I moved back from California especially if it is a super sport. Have your friend check that his insurance will cover him in Canada,when I brought mine back Progressive sent a new insurance slip with a Canadian address as if you have an accident he can be SOL.
The issue is that the being stopped with a US registered bike with a canadian license rider is an issue as the cop will think you are pulling a fast one trying to save on insurance you will have a hell of time explaining it Unless you have switched bikes and are riding together I would advise against it speaking from experience.
Interestingly I rode with Ontario plates in California and did not get pulled over once.
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