I have export-imported cars across that border several times. Because you are looking at a car more than 15 years old, there are no regulatory requirements to meet; you don't have to go through the Registrar of Imported Vehicles. You have to fax the title to the US Customs and Border Protection office at the border crossing you intend to use, at least 72 hours prior to arriving at the crossing with the car. Make sure to get a confirmation of successful fax from the machine you use. Then show up at the border crossing (it
must be the same one you faxed to), go into the US Customs office and present the car's original title. They'll stamp it for export. Then get back in the car and cross to the Canadian side. When the guard in the booth asks what you are bringing in, open your mouth and do not stop talking until you have listed
every spare part and
every bit of repair or upgrade work you had done on the car between buying it and bringing it into Canada. Do not omit anything or you will be sorry. You want to make sure you have
complete documentation. That means you need the US title, the bill of sale, every relevant receipt (new tires? Repair work? All of it) and any and all other documents related to that car. If the seller includes extra parts, make certain he itemises them in writing and clearly states that they are included in the purchase price of the vehicle. You'll be directed to go in to do the paperwork. They'll assess 5% GST but no duty. Pay that, truthfully answer whatever questions the guards might have for you, and head on down the road. If you declare absolutely everything, including the little snack-pack of potato chips you bought at the gas station on the way to the border, you should be fine. But you might run into a border guard with a bully complex, or your declaration might not be everything they think it should be, and then it's going to cost you money. Cost me $1150, for example; story
here.
But other than that unpleasantness, it's really not all that hard. Have all your papers in order, declare every last shred of kleenex and wad of chewing gum, and you'll be fine.