Regardless of how he imports the car, there are a couple of other things that are of a more immediate concern -
- He needs a valid drivers license to drive in Canada. If the US license is expiring or has expired he should exchange that for a Canadian license immediately.
- Secondly he needs valid insurance in Canada to continue to drive. He should talk with an insurance broker to see if he can get a US plated car insured in Canada. This is not to be taken lightly, if he gets into an accident then the US insurer will very likely not pay a single penny and your friend will be personally liable for any damages. While the US insurance will work as proof of insurance should a cop pull him over for a routine matter it is very important to realize that it provides no coverage. US insurers aren’t licensed or registered to provide insurance in Canada to Canadian residents, they provide temporary coverage for US residents, read your policy document for the exact terms of coverage.
With these 2 things addressed, he can deal with the import situation at a later time once the situation settles a little. If he does want to import the car, then he needs to get a fresh US visa. Go back to America, notify CBP of intent to export, then the vehicle must remain in the US for 72 hours, post which he can bring that vehicle into Canada and then complete the importation process.
If it becomes impossible for him to acquire the US visa, then maybe you as his friend can help him by taking the car into the US and bringing it back across the border. He can notarize a letter authorizing you to act on his behalf. This is somewhat unusual but not problematic. Another option to dispose of the car would be to list it for sale on Craigslist in Buffalo and/or other places near the border and American resident who wants to buy it can come across the border. Your friend can make a hand written bill of sale and sign over the title to the other person who can simply drive back with the car.