Horizons Unlimited - The HUBB - Trip from Chile to Colombia

Hi everyone,

I am planning a 4-month trip from Santiago via Argentina, Uruguay, Brazil, (perhaps Paraguy), Bolivia, Peru, (and perhaps Ecuador) to Colombia (in this order).

My plan is to buy a used (or even new) bike in Santiago, and then sell it again in Bogota (or, if that makes more sense for some reason, in Lima, or anywhere between those two cities). This tour is approximately 10'000 km (6'200 mi) long. In case this plays a role: I'm a German citizen and have my driver's license from there (as well as an international one).

If possible, I'd like to spend at most ~1'500 USD on the bike itself. By this, I mean that the difference between the buying in selling price should be no more than 1'500 USD, which means that I would be fine buying a bike for, say, 6'000 USD as long as I can realistically sell it again for 4'500 USD.

I went through many of the forum posts here regarding technicalities such as buying a bike in Chile and border crossings, but I still have a couple of open questions to which any input would be highly appreciated:

1) Border Crossings: Do you see any problems with the above border crossings for me as a German citizen, if the bike has a Chilean plate?

2) Theft: Is motorbike theft an issue in any of the above-mentioned countries? In other words: Should I rather buy a cheaper (and used) bike to minimize the risk of it getting stolen?

3) Buying in Chile, Selling in Colombia: Do you see any general issues with this process, e.g. will it be hard to sell a bike with a Chilean plate in Colombia for some reason? Also, is my idea of selling the bike for ~1'500 USD less than I bought it realistic?

4) New vs. used bike: Which would you recommend?

5) Recommendations for bikes: I've been looking into some used KL650 or Honda CB 500 bikes. Do you have any other recommendations? Main criteria for me:
a) The bike should be somewhat easy to get (i.e. not a super rare bike)
b) The bike should be somewhat easy to sell in Colombia
c) It should have an engine that won't make me hate life in the Andean mountains ;-) (i.e. I'd like it to be bigger than a 200cc bike if possible)
d) It should be comfortable enough to travel that distance (i.e. no supersport bikes)

Thanks a lot for any input you may have!

Best
Chris