Canadian with US Plated Vehicle - first time driving across border

[ycymZ]

I (Canadian citizen, Canadian residency, US License) lived in the US for a very long time under TD and later F-1 visas. I own a US-plated vehicle, and my friend (US Citizen, US License) and I wanted to drive up to Canada for a short visit to Toronto. Vehicle is registered in my name.

If I give him a notarized letter of permission of use, can he drive my vehicle in Canada? Will the fact that I am a Canadian citizen cause issues? What if he drove it across the border and I walked?

Thanks for the help.