I applaud the owner's patience, and ingenuity but as John quoted from the original article he said #1- insurance is hard to get for a wooden boat, and then later said #2 that he couldn't afford insurance.
Maybe you can't insure the boat, but he should be able to purchase liability insurance. If no one is willing to issue him any kind of insurance, then he should take greater precautions than normal to insure that his boat doesn't blow down on anyone else's property. This is sort of a case of someone biting off more than they can chew.
I'm not trying to crap on the guy, I'm glad for him. I just hope that he takes greater care in the future to secure the boat against adverse weather.
The other thought that keeps rattling around in my brain is: "Who the hell keeps a pleasure sailboat that draws 8 friggin' feet in the Chesapeake Bay???" That thing belongs in Puget Sound.