As far as medical insurance is concerned we got a world wide cover INCLUDING USA AND CANADA from our home country.
Bike insurance for Canada and USA was through Motorcycle Express (Google). Mexico was through Lewis and Lewis (California - fully comp). Central America was at the border - usually obligatory but not always, if it is they will tell you.
Apart from that you can just go - best resource is IOverlander app for borders, don’t go to a border without checking it. Take original of your bike reg document, make copies (B&W) of passport, license, bike reg - you won’t always need license copies but might need 2 of the others so take plenty.
There are some idiosyncrasies for the odd border so I can’t emphasise enough the importance of checking IOverlander as things change.
I can recommend Overland Embassy for crossing the Darian Gap.
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