I see no possible harm coming to "the Chilean people" from a transfer of a foreign bike, not based in Chile, never sold in Chile and which is legally taxed, insured and registered in it's home country and has a current TVIP for Chile.
If a buyer "fiddled" the title or TVIP but then insured the bike based on that "new" information, I don't see the insurance company having a problem as long as premium has been paid and new owner is the policy holder and can present title when buying said insurance policy. Insurance companies don't do title histories ... why would they?
And last I checked ... Chilean transito Police are not experts on Foreign Titles or Log Books either. If everything matches up ... that's it. Good to go. Everyone is covered.
The fact is that stupidly complex rules are in place that impede the free flow of commerce and limiting a travelers options ... it's this that really hurts the Chilean people most of all.
It discourages moto tourism and drives tourists elsewhere. Like the borders in Cent. America: Thousands just "go around" rather than run that gauntlet of corruption and insanity ... or they blast through in a day ... and vow not to spend even on dime there.
Allowing true duty free sales ... and making it easy for tourists, charging very reasonable fees, could be a boon to Chile's tourist economy. (but I doubt they could organize it properly ... never happen ... too many selfish interests at play)
If you'll note, I also suggested that the seller would have the option to process the sale of his vehicle through his local home country DMV (or equivalent) and transfer title to the buyer. That makes it legal.
In California ... this can all be done via mail, no need to show up at DMV. I'm sure other agencies are similar. But what is legal is EU or USA does not necessarily make it legal in Chile. Better to try a couple $20 bills instead.
I would agree with paying Chilean import & sales tax on a sale IF:
1. Bikes where to be permanently imported into Chile.
2. They were Chilean based bikes being re-sold (sales tax) to permanent resident of Chile.
A foreigner in transit should not have to pay import duties or sales tax if leaving the country within a certain period of time. No idea what Chilean law says about this point but seems fair to me.
But in the case of foreign TVIP registered bikes in transit, owned and sold by NON residents ... IMHO ... it's NONE of Chile's business what happens with these bike as long as TVIP fees have been paid, bike is insured and owner has not overstayed Visa. These bikes are not even officially in Chile ... they are temporarily there ... basically in transit.
IMHO, this sort of sale should be done between buyer and seller only ... they don't really need a Free Trade Zone at all.
But obviously the current arcane and counterproductive rules will continue ... do they still use 5 sheets of carbon paper for everything?

Computers?
Sounds dangerous to me! !Copias! !Mas Copias!