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Unless your boss has a horrible record I'd tell him to look for a different insurance company. I know guys who are 25 and own and insure corvettes 
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I agree. I've owned a vette since I was 17. Its an old one, but probably worth more than most 92-96's. Sure insurance is expensive, but its not impossible. If he has money for major body kits etc, I don't think there's a problem (w/o past tickets at least).