From USA down to Argentina, until today the situation is like this:
Mexico: you can buy online at https://www.bajabound.com/
Guatemala: not mandatory
El Salvador: not mandatory
Honduras: not mandatory
Nicaragua: shop at the borders (roughly 15 USD for 1 month)
Costa Rica: shop at the borders (around 50 USD for a car (cheaper for motos)
Panama: shop at the borders (roughly 15 USD for a month)
Colombia: They sell literally everywhere in gas stations or agencies.
Ecuador: not mandatory
Peru: shop at the borders or agencies in cities
Argentina & other MERCOSUR countries: You can contact with the local office of MAPFRE. They were happy to send me a quote that covers you in MERCOSUR countries.
In any case, you can always advise iOverlander (web & app) for the latest updates, border crossings info and locations where to buy in big cities/ towns.
Good luck ;-)
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