Great idea man! Except maybe Venezuela..... Passed through there a few months ago, not too impressed with security at all. And the cops tried to steal my shit all the time, really. Army was not as bad though. Petrol is really cheap too, can't argue with that...!
Colombia (Bogota) on the other hand is a pretty easy place to ship a bike to from what I've been hearing, and a very safe place too (I spent 5 months of a year in South America there, never a problem). Gorgeous country too, and lots of friendly locals. No worse street crime than many western countries.
Quito in Ecuador is the only place I'd say to watch your back really. All in all though I never really felt unsafe, just take the usual precautions, all will be well.
Keep in mind the seasons dictate where you start or when. Right now it is winter in Patagonia, turning into spring. In a few months is the perfect time to start down there with summer coming in. A few months later you do not want to be down there on a bike.
Whatever you do, it'll be the right choice. Enjoy!
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