you REALLY should insure your boat - at least liability and ESPECIALLY if you race it (even once a year). It's cheap (my 2004 Nacra F18 costs $181 / year for FULL coverage including sails and the trailer).
I was involved in an incident a couple of years ago that totalled a Hobie 18 and my Nacra 6.0NA...I certainly don't want to run the risk of paying for that out of pocket (just imagine if anyone gets hurt!).
Here is the thing though.......... I have been in the insurance world for years and years. I have had to take more actuarial courses than I care to remember. If the cost/premium is relatively low then the insurance company's actuaries have looked at years and years of statistics and determined that the risk is relatively low as well. I look at insurance this way...... I could insure against EVERY loss if I wanted to but it is too expensive to do that. Therefore, I choose those risks I feel are VERY Unlikely and/or easier to recover from and self-insure those. You COULD buy shark insurance if you want. Everyone has heard of someone getting bitten by a shark but no one (I shouldn't say no one because I know someone who did buy it!) buys it. It's cheap too.
Pet burial insurance is one of the fastest growing types of coverage. You tell me the sense of that!
Having said all that, I guess I will look into the liability coverage. Probably stupid to not have something that could protect all my possessions. (Really it's not protecting my possessions though,right? It's just providing the dollars from another source.