speaking of Chili
it was chilly here in the New Mexico desert last night.......
I know you can also buy in Peru, but don't need to return every 6 months, Ecuador too, and I'm pretty sure Colombia. Bikes are more expensive in those countries though, Chile is the cheapest as I remember.
You can get MercoSUr insurance which covers you in most SA countires, the only time I was ever asked for insurance was in Colombia, 4 -5 times in 4 months, might have changed since then.
It is possible to sell a Chilean bike in Peru, but you have to pay baksheesh.
NOT in Colombia don't try.