Once you get the bike out of Chile you can really do whatever you want with it and you will always be able to take it back into Chile at some point in the future.
I tried to cross from Chile to Peru at Arica and they would not let me know matter how hard I tried. I had to return to cross into Argentina then come up through Bolivia to get to Peru and eventually re-enetred chile from Bolivia (RIDE THE UYUNI DESERT!!!!)
I crossed MANY times down there and really it all depends on the situation. You know all the documents you need and having all those will help but my best advice: Leave Chile to Argentina and then take it up into Bolivia > Peru > wherever and eventually come back to Chile. The hardest challenge you are going to find is getting the Chilean bike out of the country without an issue. Also - you can legitimately cross Chile > Argentina > Chile as many times if you want in case you want to travel south.
i've also head brazil can be a bit hard to get into / deal with....
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