I had a late 70's 20 foot sailboat that I paid only $1000.00 for in '91. Because of that, I didn't insure it. My reasoning was I would never do anything stupid enough (and I never did) to warrant needing insurance; I knew how to sail, I grew up on boats, added a VHF, depth sounder and Loran. Component failure never occurred to me. One day back in '97 a lower shroud snapped while close hauled. The mast proceeded to fold in two and fall over the side. Unfortunately having just got married and bought a house, I had no cash to buy a new mast. If I had insurance, I could have afforded the deductable and bought a new mast. She sat behind my garage until last summer when I finally sold her, mastless.
The only good thing out of all of this was it showed us we needed a bigger boat. We now have a 38 footer.
Catalina 38, Hull #112
Grosse Ile, Michigan