Nor trouble for Canadians in a Canadian rental driving into the US. I found out trying to book a Zipcar in Seattle to drive a bunch of stuff to Vancouver that, as a Canadian resident, I can't drive a car with US plates into Canada, per Canadian customs. That if I stole a Zipcar or rental car would get me into a lot more trouble than trying to avoid taxes/duties doesn't matter at all. (I couldn't do it the other way around, because the Zipcar allowance for US cars is 200 mi/day, well over a one-way trip, and the allowance for Canadian cars is 200 km/day, which doesn't work.) Yes, they need to issue you a Canadian insurance card.