I paid about $120 for my policy (just renewed this month)that includes the standard stuff (liability, Property damage, etc.) and limits. To save cash, I chose a high deductible ($1000) since I figured I would only make a claim for a total loss/theft anyway, and budget for replacement stuff (sails, mast, rudders, etc.). If you make it a year without major damage, you usually end up with enough spare/replacement parts to sustain anything but significant hull/sailplan damage. Chalk it up to "cost of operation", and save your insurance premium dollars (which you could buy parts with).

Theo- a few benefits of your insurer:
1) They cover racing (a lot of insurers exclude that)
2) They offer "replacement cost" coverage - basically, they pay what it would cost to buy a similar boat if yours is a total loss
3) They offer a sliding deductible. If you don't file a claim, they drop the deductible amount at renewal 25%. My original deductible was $1000, but I think it's down to about $600-700 by now.

I've suffered some damage to the boat (ripped sails, broken battens, holes in the hull), but fixed them myself or sent them to my local dealer/repair facilities. I had it fixed to my specs and on my time schedule, which I felt was a better in the short term... I'd rather fight with the insurer in the total loss scenario than just trying to get little stuff done.

I believe you met Ryan at Eustis, who suffered a MAJOR breakdown this season (split hull, broken mast, torn sails)at Hagar's Run, and his insurance company did him right. He'd be a good source of info as to how the process works.