To clarify, my intention is not to make this car a daily driver, but it will see use like a typical classic. If I take one of my cars to a cruise night, then he can follow along in his car to join the show. He can wash and wash it, and work to learn that hard work can result in great results. I know American RWD V8 cars like the back of my hand, and this particular car (never seen winters, owned by a very close friend) was a good buy. Plus it only had the weak LG4 engine with a whole 145 hp, but a 5-speed so he could learn the lost art of rowing gears. There would be very strict usage rules in place for him. I want him involved in the car culture, it's something I want to pass down to my kids. He loves classics like his dad and is always eying up his first car in the latest AutaBuy. An old Camry would make a great winter beater/daily driver, but I can tell you, no kid is going to get excited over a transportation appliance like that.
As someone who has grown up with classics, and currently owns a couple, I am full aware of the inherent safety risks involved in operating them. You should probably chastise me for allowing my kids to ride around in my old cars, even when they were infants, albeit in a modern car seat, installed properly (I took used volunteer to train people on installs). That said, it is okay for a 16 year old to ride a motorcycle in this province, which is certainly much higher risk than a 1980s car. Kids here can also ride 4-wheelers and snow machines, both of which I am sure have much higher fatality rates. Life inherently has risks, and I am pretty sure teenagers do a lot of things more risky than driving a vintage car.
On the insurance, my broker is looking for me. I am not optimistic. The rules for insurance are set out by the province, not federally. However, I am pretty confident it's not a rule against doing this, it's just that the insurance companies don't want to take that risk. Even the arbitrary 20 year old rule makes no sense. My dad daily drove a car until it was over 30 years old without issue. They also are under the impression that all old cars are rust buckets and shouldn't be on the road - which is definitely not the case.