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I was confused. I didn't understand that you hadn't been in an accident.
Honestly, I'd never try to file a claim like that with my insurance company, and I've never heard anybody doing it. That'd be like asking them to fix rust, as far as I'm concerned.
If you love the car, that's great. Get the paint and headlights fixed and keep driving it. But I wouldn't ask the isurance company to pay for it. I would think you'd just be paying for the next five years with higher premiums anyway.
Actually, the most important part of a paint job is the prep. You could save yourself a lot of money by learning to do that yourself. As for the headlights, I bet that using something abrasive enough you could strip the pitted plastic off them and then polish to a nice shine.
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