Auto Insurance for an old car and young driver

Back in 2011 Safeco had no problem insuring my 16 year old son in my 1975 2002. It had no electronic nannies of any sort, but I did install new 3-point seat belts, E21 Recaros and I made sure that the drivetrain, brakes and suspension were in excellent shape.
More importantly, my wife and I agreed that spending two days at the BMW Performance Center Teen School and another day at Street Survival was a better strategy than tottering around with no driving skills in a "safe" car.
Despite the pronouncements of doom from the hand-wringing bed wetters he survived just fine.
 
I don't disagree with pointing kids toward safe cars; however, I'm always trying to wrap my head around parents buying their kids expensive cars in the name of safety. To cover that base, we sent all three of our kids to a stringent defensive driving course, which included inclement weather driving, handling breakdowns, etc. This was in addition to standard driver education in their schools. None of them have a single ticket or accident in their histories. And our oldest has been driving for over a decade.

For his first car we gifted him a very nice 1989 Plymouth Sundance. He still has it, everything works, and his insurance rates are actually quite low. No payments to weigh him down early in his career helps a lot. And he really likes driving something that's fairly unique these days.

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Newer cars are inherently safer than 20 year old cars-that's the comparison in this thread. If you can afford a new(er) car for your kid-and the insurance that goes with it-there is absolutely nothing wrong with protecting your kid as much as possible.
 
Has anyone ever run into issues getting insurance for an old car and a young driver? My son will get his license in a few years and grew up around my old cars. He and I wanted to by a project car to work on for when he turns 16. A friend is selling a clean 85 Trans Am but my insurance company won't insure anything over 20 years old. I called my classic car insurance and they won't allow any drivers with less than 10 years experience drive a classic. So not only can't I buy a project car, I can't even let him drive mine! This is ridiculous! All my cars as a kid were over 20 years old and I learned to drive on my dad's classics.

I am still shopping around but not overly optimistic. Has anyone experience this problem? Anyone in Ontario have an occasional young driver on an old car?
I started driving with my permit in 1997 and got my license after completing drivers ed in 1998. My first car was a 1982 honda accord hatchback so the sane age I was. Is there any kind of exemption that you could sign? Ahh ok make a scene and they'll "allow it." Sometimes you have to push back a bit. Good to see it resolved.
 
Back in 2011 Safeco had no problem insuring my 16 year old son in my 1975 2002. It had no electronic nannies of any sort, but I did install new 3-point seat belts, E21 Recaros and I made sure that the drivetrain, brakes and suspension were in excellent shape.
More importantly, my wife and I agreed that spending two days at the BMW Performance Center Teen School and another day at Street Survival was a better strategy than tottering around with no driving skills in a "safe" car.
Despite the pronouncements of doom from the hand-wringing bed wetters he survived just fine.
Thank you. This is what my plan is too. Good driving skills are in valuable regardless of the vehicle being driven.
 
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