I would say Colombia.
Bye a new one. Travel around.
Sell it again in Colombia when you are done.
Easy and legal.
Than you won't have to spend a lot of effort with the purchase and selling.
And can use the time driving.
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SA is giant.
The goal to visit as many countries as possible ??
Maybe not the best. Take time to find and stop at all the beautiful places.
Go off the main road and discover. Would be my advice.
But it is your trip. And you will enjoy, whatever you do.
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Apache are Indian made bikes. RTR 180 and others
AKT are Chinese made bikes TTR200/TT 250 Adventour and others
https://www.tvsmotos.com/motos/apache/apache-rtr-180
https://www.aktmotos.com/motos/todot...-250-adventour
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From Colombia your are going into Ecuador.
In my view a very underrated country. Because people just pass on Pan American.
It has everything within a small area.
Beaches by the Pacific.
Green agriculture a bit from the coast.
The Andes. Nature and culture
The Amazonas (El oriente) on the other side of the Andes