Just did this exact same thing last summer - bought a '69 Camaro from an owner in Toronto. Met him at U.S. Customs at the border (he trailered the car), produced the bill of sale and Canadian Registration, and for $5.00, Customs provides you with an Informal Entry Certificate; this, the bill of sale, and the Canadian Registration is all you need to license the car in the U.S.; the Informal Entry Certificate tells your DMV that the car has legally entered the U.S. - otherwise they won't touch it.
If the car was sold new in Canada originally, you can contact George Zapora at the "Vintage Desk" at GM of Canada Headquarters in Oshawa, Ontario, give him your VIN, and for $35.00 he will provide complete original documentation for the car
including the day it was shipped, the dealer who sold it, the order number, and a complete rundown of all the options that were on it when it was built. You might want to do this ahead of time so you can compare the car's REAL history with whatever the current owner has told you. George can fax the info to you withn 48 hours, and the hard-copy stuff will show up about three weeks later. If it hasn't been restored or poorly re-painted, you'll find a white GM of Canada sticker on the right inner fender just forward of the heater hose clamp that lists recommended oil quality and change intervals. Other than the oil sticker and an English-French warranty pamphlet, it's exactly the same as a U.S.-sold Camaro.
No import duty or taxes, as the car is over 25 years old. Call ahead to U.S. Customs at whatever border crossing you plan to use, explain what you're doing, and they'll verify exactly what they need. You'll find Customs is busy as Hell with commercial trucks with brokered loads on a weekday - try to arrange the meet on a weekend - the Customs agent will tell you the best time.
Make sure the Cashier's Check or whatever you use to pay him with indicates clearly that the amount is in U.S. funds so he doesn't have an argument with his Canadian bank when he gets home.
Check the car very carefully for rust - they use a lot more salt up there than we do. Mine was never driven in the winter and was stored indoors for 15 years, so I didn't have any problem. Good luck!
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