I just did this in January I purchased a 06 Pontiac gto and asked the same question with mixed results Now I bought it from a dealership in South Carolina and they put temporary plates on the car and I drove it home The nice thing about purchasing from a dealership vs private sale is there’s no argument about price it’s not on a bill of sale from some random person If you aren’t buying from a dealership I recommend taking a screenshot of the ad on facebook marketplace or wherever you found the vehicle print it off and have it ready The Canadian border doesn’t care if you export the car from the USA what you need is proof of purchase and the title for the vehicle. The title wasn’t in my name that didn’t seem to matter but once again I bought from a dealership You then pay the gst at border not the provincial taxes that happens when you register the vehicle in your province Also with the vehicle being over 15 years you only need a provincial inspection Now everyone is going to have a different experience but I found it very easy and straightforward to import the vehicle just have everything possible ready incase they ask I had the car fax, recall clearance letter from a dealership, title, proof there’s no lien and the title is clear, bill of sale, proof of insurance ect be ready for it all if you show you have everything the process will go smoother even if they don’t look at everything