I paid cash for my 2001 CR500, but I still have it insured. It's $6/month for comprehensive.
Also, the gear is a good idea. Here's some images from last weekends ride, note the use of protective gear (I'm on the far left, same bike as my avatar). Also, you can't see the kidney belt and Thor Force kneeguards I wear, but they are there.
20+ CR500s firing up is deafening.