I'll assume you dont insure your car then?
How about you personally pay the difference between what he paid for it and the Market Value? Put your money where your mouth is. ;)
Why do you keep your car rather than just hold onto the market value in cash? Is this just an investment for you? If so, why not play the stock market. I'm not buying your attitude here.
My Dart has liability coverage on it, as required by US/State law. If anything ever happened to it, I'd spend as long as it took fixing it. So what's your point?