A few stay in the water year around here. Mostly it's due to lack of funds and or neglect. Amazingly, the moorings hold up to quite a bit. This storm was Nov 1. Only two boats remained in the water, the one with the shredded headsail and the bigger Hans Christian type. Both made it through the winter but both are valueless boats today(liabilities, actually).
A lobsterboat or two always stay in. The storms slowly wear the mooring gear down (shackles, hawsers, etc).
This 'one' stays in every year. A couple seasons ago it became a problem for the owner. The ice began pulling the caulking out of the seams. She'd take on water and the auto bilge pump would keep up, until the battery died. Then he would have to get out to it.
There was no one to assist them if the men fell through the ice away from the wharf. So they dragged the dinghy out with them and swapped out a charged battery.
All in a days work,...
Come spring though, some part of the mooring let go. He moved it to an inner dock....
Then the docks bull rail (where you tie off) let go from the dock. He's a fisherman, not a dock builder.
The boat (and his dock) floated across the bay and fetched up on an island.
'She's' out in the harbor on a mooring right now.
'She' is the third fishing boat this guy has owned since I've lived here. Insurance? Ha.
He's a nice guy and I have a lot of respect for him, it's tough work. He's tough on boats but he's very kind to his dog.
(this was his first or second boat, I've lost track).