Costs can vary a lot
When I resided in a coastal town, moorings off the town dock cost $50 per year and that included permission to leave a dingy at the dock. Of course, only the ugliest dingys were still there in the fall, but mine were deemed not worth stealing. Transporting on a trailer and storing our Catalina 22 beside my house was cheap. I could winterize the outboard and I changed standing and running rigging myself when it needed it. That left a few hundred at most a year for sandpaper, bottom paint, varnish, etc. , and liability insurance. If there was any threat of a significant storm, I pulled the boat. So, insurance risks were quite low. It would be a bad year when total costs exceeded $500. My cousin sails his West Wight Potter for even less than that from a mooring in Lake Champlain.
On the other hand, friends spend ten times that to get premium service and do no maintenance on the boat themselves.
Bigger is not necessarily better. When I used to have multiple boats in the water (it was really cheap) the smaller boats were used about twice as often as the big one because almost every trip was a day sail. We laugh about it, but I have a brother-in-law whose 50'er rarely leaves the dock, and his cost per hour of actual use is not funny at all.