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I hope he doesn't do it that way, because he's going to get stopped at the border and it's going to be a big mess... you have to buy it as if you are pretending you don't know him in order to complete the entire process properly.
If he goes to the border and tells Canada Customs he's selling the car to you in Canada they'll be like "Okay, well, where is he? Did you tell U.S. customs a car is laving the country etc. etc."
Likewise, if he just drive through and sells it to you, if you go to register it U.S. Customs is going to be like WHOA there, we never heard this car left the country, uhm, bring it back because it was illegally exported!
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