My Israeli buddy has just flogged his Chilean-registered Euromot (bought new in Santiago) in Colombia (illegally of course) having ridden up through Bolivia, Peru and Ecuador. He had no probs at the borders - but he came through Bolivia into Peru.
Also met an Aussie in Cusco who had bought a second hand car in Chile and driven it north.
Can't say you can cross the Chile / Peru border, but you can clearly get through Bolivia - and this is a much more enjoyable route north.
Cheers
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