For the new buyer to register in Chile the previous owner needs to be present so unless you could have someone 'impersonate' you I don't know how you'd go about this. Chile is quite organized and your details would be computerized.
As for returning to Chile vehicles are checked out and in by your RUT number not the passport so I'm not sure if you flew into Chile what problems you'd encounter. Likewise if you just said it was stolen or fell into the sea what could they do? A fine? I don't know.
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