I remember from my last trip to the US that it was always a good idea to get onto the Interstate road a few miles before crossing state lines, the reason being there was ( always, it seemed ) incredibly well-equipped welcomimg centres, with an amazing wealth of information and help - mostly free.
Otherwise, even the smallest of towns had a 'Chamber Of Commerce' which again doubled up as a tourist office.
As to the bike, there are normally a few options. Is it practical for your friend to take the Canadian test? ( It was very easy and quick for me in the US ) If so, the Canadian license will solve ALL problems!
Another option is, as you say, for you to officially own the bike and put your friend on as an additional rider. Your Canadian insurers may load the premium quite a bit, though.
Finally, phone around. I was getting the big no in the US ( unless I had the license, they said ) but eventually a broker made a bit of effort and got me a quote on the British/European license.
I'd be amazed -truly amazed - if a Norwegian company will insure the bike.
Hope it works out!