In my teens during the 70's my Dad had an 18' Penn Yann just like this.
He had it on a mooring in the Charles River near the Mass. Ave. bridge. That was a different era in Cambridge before it became the peoples republic. I don't remember the exact fee to get a mooring but it was cheap by today's standards, something like $20. It originally had a 50HP Evinrude but one day we went to go out and noticed the boat floating a little odd. Turned out somebody had stolen the OB right off the boat while it was in the water! That was the end of the mooring and the season. Over the winter he found a 90HP Johnson that really made that boat move.
Best memory on that boat was watching the bicenttenial fireworks in 1976 with Arthur Fiedler leading the Pops concert. When I was old enough to drive he let me trailer it where ever I wanted and eventualy he basically gave the boat to my brother and I. That lasted several years but sometime in the early 80' my brother ran aground and busted the bottom up. Without me knowing about it the boat eneded up in a bonfire on Whitehorse beach in Plymouth MA on the night before the 4th. I still get worked up thinking about that.
My mom worked at Harvard U. and one of the benefits back then was that they gave employees and their families access to the recreational facilities. This included the sailing club so from high school to my early 20's I sailed O'day dinghies and Lasers there. They also had a Soling but it was rare to get to use that. It was weird, a poor city kid hanging with Harvard students but some of them really used to look forward to me showing up because I had, uhh, local knowledge of access to supplies of recreational drugs.
After I moved west of the city in the mid 80's I had at various times:
A 12' aluminum skiff with a 8HP motor.
A Super Snark sailboat.
A canoe.
Five years ago my ex-boss gave me his fathers old 13' Whaler with a 25HP Evinrude.
Three years ago I bid $750 on a 17' Wellcraft/Manatee on ebay. Here's a picture of the two together.
Two years ago I bought my current boat for $2600 then sold the 17' for $1200. Also that year I gave my ex-boss the Whaler back. Long story why but I'll just say I miss that boat.
That's it. I'm happy with the 250 right now,however I would like to replace the Whaler with something similar but that's not in the budget right now.