Re: Insurance and cruising...
I've got mixed feelings on this.
A couple of years ago someone sailed a boat into a local harbor and anchored in the middle of the mooring field which started a game of bumper boats. The harbor master had him move. He came back later, and tied to a loading area on town dock and left the boat. The harbor master again had him move. Then he went out into the bay and dropped his anchor straight down before a storm, zero scope and rowed ashore before a gale. The boat of course didn't hold and slipped about 1/2 mile across the bay into some docks and destroyed them. He had no insurance, the boat had no salvage value, the owner was broke. Costs fell to the town, the owner of the dock, and those who do buy insurance. These costs including towing away and disposing of the guys boat that was hard aground with remains of the dock wrapped around it.
A few irresponsible individuals mess it up for everyone. I am sure there are stories on the other side of people with insurance that abuse that.
No easy answers.
That said, I've never been asked for proof of insurance as a transient, but have been consistently asked when operating out of a marina seasonally.