Put simply, from the moment that you enter Latin America i.e. Mexico south to TdF, you need third party insurance for your moto. It is not a legal requirement in all Latin American countries BUT and it is a big but, if you are involved in any sort of RTA in the region, a law based on the old Spanish system comes into effect which basically says that if the cause of the accident cannot be admitted on scene then all vehicles are impounded and all riders/drivers taken into custody until a judge can get round to allocating blame. Older European members of HU will remember the need to purchase a 'Bail Bond' in addition to a 'Green Card' when visting Spain pre EU membership days. In CA and SA insurance can usually be purchased at the point of entry into each country or in the first town over the border but when you enter the Mercusor area, (Argentina, Bolivia, Brazil, Chile, Paraguay, Peru and Uruguay.), insurance can be bought to cover the entire area. This insurance in CA and SA comes with 'Legal Assist.' which means that if there is a danger of you being incarcerated, a lawyer will get you bail. Whilst this info is correct in my experience, other members may be able to extend or amend the content. As to your other insurance question, lots of info on the HUBB in the 'Healthy on the road' section. Ride safe.