The insurance thing comes up often, and it's nothing more than a risk/benefit situation.
If everything were equal... you were an average boater had an average risk, average boat and operated in average conditions, insurance would be a waste of money in the long term.
I could argue, if one had a number of items to insure and spent a strong effort on avoiding an issue they would come out WAY ahead without insurance.
Another thought.... if you self insure:
you don't worry about deductibles
there is no hassle with the insurance companies
there are no policies with fine print
you don't have to go to court to get justice
there are no attorneys
there no need to create and maintain a value list of the components and their value and pictures
And, in some cases you can deduct the loss as a casualty loss. (See IRS Publication 547, form 4684.)
So, what's the chances you'll have an accident? Just raw stats, including EVERY boat is once in 285 years, and that loss would be $1,085.65. Now, our boats are most likely a LOT more expensive than the average, but crash a LOT less than average. If we factor in how many boats 40 to 65 feet have accidents and the percent that are out there it's about 20 times safer than the average.
The point being, is that you're VERY UNLIKELY to have and accident, and significantly less having a total loss.
BUT and here's the BIG BUT...... IF the boat is a substantial amount of your net worth, perhaps your home and that's most of what you have, a total loss will put you out of business permanently. You will likely die before getting the benefit of the "time between total losses" makes you whole. And that's a risk most folks aren't willing to take.
So, it's a very personal thing.