I also think this is an unrealistic idea.

The problem is customs and import taxes/ fees. Most countries try to protect their automobile industries by making it expensive to legally import vehicles from other countries.

The other main problem is "time." Have you ever tried to sell a foreign registered vehicle in another country? It is a nightmare! Every buyer is afraid to touch it with a 10 ft pole because of legalization issues. Think about the month of time that you will likely spend trying to sell the motorcycle. It is a much better idea to sell it for pennies on the dollar and spend that month of time working back at home.

In my opinion it is a much wiser idea to start out with an economic/ utilitarian motorcycle like a KLR or an air cooled DR 650 that you do not have to worry about losing much value on the sale.
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If you have any interest in exploring South America I have a good cost saving idea for you. Plenty of Hubb travelers end there motorcycle trips in Argentina and descide to sell their bike's for pennies on the dollar. If you flew to Argentina, you could kill some time by doing some bus tours and keep your eye on the Hub for sale section for a traveler selling their foreign motorcycle in Argentina. There is a way that you can avoid having to pay and customs/ import fees if the seller agrees to help you out and cross the border to Chile with you.

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http://www.journeyrider.net Latin America blog (07-8)