Hi Bazza,
I done a trip in 2018, from Edmunton in Alberta, into B C, crossed the border into Montana and done a big loop of the states and back to Edmunton.
I started off on "kijiji.ca" and got a feel for what's on offer. Seems they rate Harleys very highly and the Jap stuff much less so. I ended up buying a V Strom 650 fully loaded on this website, rode it for 7500miles and sold it at the end for about $450 less than I paid for it. All worked out super. If you know someone in Canada, their address helps. Don't let anyone tell you this or that is not possible... I even got a company in Florida to insure me in Canada on a Canada reg with an Irish licence, breezed into the US with no questions at all!.
Ref. the bike, the V Strom was lacking speed, seems most vehicles move along at 70mph and it was'nt fast enough to overtake safely. I'd be looking at a 1000cc VStrom or similar when I do the next venture over there.
Tom