Ive been looking at prices in Chile, and they dont seem so bad, compared to Denmark (we have up to 170% markup registration tax on some vehicles, I dont know if it applies to motorcyles).

I dont know whether I need to register and insure the bike(s) in Denmark and then ship/air them to an SA country. We will also look into germany as its just a hop across the border.

But regarding Chile, the problem seems to be time, we dont want to spend 1-2 weeks unless we have to (I dont know how long it will take to ride the length of chile, as I noticed you can get the printout at any civil registry office for international travel).

Also I noticed currency wise, would we be able to JUST use USD from chile all the way to USA? It seems odd (from a european standpoint).

At this point price is 2nd on your priorities, time being the first.

I was told in Brazil it will take 3-5 max to buy and register a motorcycle there for around 100 euro (compared to 60-70euro +- 1.5% of motorcycle price in chile), although the motorcycle might be more expensive.

On another note, what sort of motorbike should we look for to ride? I see KLRs are propped up a lot but those are too expensive I think.
Are there any brands or models, or makes that are cheap, reliable and easy to fix? Or should I look for something between 150 - 300 cc?

Unfortunately I am very new to traveling in SA, and Ive never owned a motorcycle (I have to learn to drive before I go too). So I might have my priorities the wrong way around, or missing stuff.