Quite a few elect to buy compulsory insurance when they first cross the border of each country. No policy required for Ecuador at the moment. Possible to get insurance that covers all the southern countries as a bloc. Three or four countries - Mexico is one - do not recognise any external providers and you must buy it from approved providers either on-line in the case of Mexico or at or near the borders..
Woodalls Open Roads Forum: FAQ Insurance for Mexico discusses it pretty well and there is also info available under the "get ready" item up the top on this forum.
Some US insurers - ie Progressive will extend coverage on their comprehensive policy for driving in Mexico but you still have to take out the Mexican liability one as well. Some Canadian companies may have similar deals or will rebate your premiums for the time you spent in Mexico.
There are a few borders - La Balsa between Ecuasdore and Peru, and Copacabana between Bolivia and Peru is another, that do not have insurance available and then you would be forced to run the Police gauntlet for several hours to the nearest agency
Might also be some info in the Central America and South America forums, or trip paperwork forums
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