Colombia to Argentina (Nov'18-Feb'19)

[p.mat]

Hey Guys,

Firstly wanted to say hello as I've been a member of the HUBB for quite some time but so far mostly reading it on and off without much writing. Now that I am preparing for a trip to South America soon, I was hoping I can ask for some expert advice from you guys!

I am planning to fly into Medellin, Colombia beginning of Nov'18, buy a motorcycle there (considering KLR650 or similar) and ride it along the west coast of the continent (via Ecuador, Peru, Bolivia, Chile, Argentina) all the way to Ushuaia by end Jan/beginning Feb. If time permits I wanted to do a week-long boat trip to Antarctica and either sell the bike in Ushuaia itself or ride it to Buenos Aires and sell it there before I take a flight home end of Feb'19.

I am thinking of following a route similar to this. The map under the link is not mine (borrowed it from the website of a tour company organizing SA trips) and I expect to take other roads based on local recommendations etc. but it should be close enough to give you an idea.

My Spanish is very basic so I'm still not sure if I should buy a bike from a fellow traveler (if I am lucky enough to find one in Colombia), Mercado Libre or get it through a second hand dealer to arrange all the paperwork for me (I read this post and it seems that the formalities are quite complicated without knowing the language well?).

I've also read that selling the Colombia registered bike in Argentina can be pretty complicated (and permanent import is ridiculously expensive) so I am thinking of either doing a border-crossing sale on Argentina/Chile border or in the worst case scenario getting the bike officially scrapped at the end of my trip (though it just feels wrong so will really try to avoid this option...).

Would be really great if you guys could share ANY thoughts or suggestions! Every comment will be much appreciated!

Cheers