$100 which if you win will usually be paid back to you.

If you're the cyclist who gets the door prize or get hit why would your insurance have anything to do with it? You'd sue the driver, who would then immediately send the claim off to his insurance company, who would defend the action.

Is it more trouble than it's worth? I guess it depends on the situation. If you smashed up a wheel, I'm certain you can get some nice quotes from the bike store folk on the board and do alright.

All of this is based upon the fact that you weren't running a red light, or doing anything sketchy. it also would need actual damages, not just the normal every day squeezed too close to the curb for comfort.