Re: o'day daysailer III
Should be a great experience. I learned on a DS1 on the Rhode/West rivers. I believe the DS2 and 3 have self bailing cockpits which is a big advantage over the DS1. I was always a little concerned of capsizing and needing a tow to the closest beach bail it out.
I mostly singlehanded it. So, I added a jib downhaul so I could easily douse the jib without leaving the cockpit. Everything else was already run to the cockpit. I also added a Holt Allen Nylon Jam Cleat to the tiller with a piece of 3/8" shock chord between the stern cleats to make a simple/cheap tiller tamer.
It was also easy to drysail so it was inexpensive to keep it at a marina. I quickly learned that stepping the mast was not going to be fun each time I wanted to go out. You may have a tabernacle...