Registering a R32 Skyline in Canada and keeping it in the U.S.?

You're dreaming. It's illegal no matter how you cut it. Move on. .

I fail to see how this is "beating the system." If you are from the US, you need to import the car into Canada before you can register it. That will cost a couple of thousand dollars -- environmental fees, metric instrumentation conversion, installation of DRLs, inspections, import duties, environmental fees, VIN checks, title searches, etc. You then have to get the vehicle insured to get Canadian license plates. You have to show proof you are living in the province (typically a provincial driver's license, student visa, etc.). In most provinces that will cost you at least as much as having it insured in the US and probably extra since you have to pay extra in order to be covered with the higher liabilities required in the US. Most insurance policies will also limit how many days a month you can drive in the US unless you pay even more. They also give you a little sicker with the date of the insurance which you put on your license plate. Then presumably you'll have to return to the United States. I would expect the border agents to question you about entering the US with a US passport while driving a car with Canadian license plates. However, you obviously have the registration in your name. However, it's generally illegal in most states to have a car within the state for more than 90 days or so without having it registered in the state. And of course if you are pulled over, police really are sticklers for out of country and out-of-state cars for proof of insurance. I don't see how this "beats the system". You pay thousands in imports, have to somehow get a Canadian license, higher (Canadian) insurance rates, have to return to Canada every year to renew your insurance, probably aren't actually covered if there is an accident (since you lied about living in the province and are driving it beyond the number of days in the US they give you), etc. If you are going to drive around with an uninsured vehicle, having Canadian plates is just asking for the officer to check.

If it's over 25 years old, you shouldn't have any problems registering it in the US anyway...