As a re-entry sailor I'm re-thinking my old, bad habits. One of them was never wearing a PFD unless the weather was really rough. 'Corse we didn't have self inflating PFD's and what we had wasn't too comfortable. Now, much of my sailing will be solo and I think a good PFD and teather system will be my next boat purchase. Most of my sailing will be in the Gulf of Mexico.
My previous boat (Westerly Padgent 23) was easy to board from the water. The top of the rudder was the first step and the stern rail was an easy reach; no one ever had trouble boarding from the water. We frequently "trolled" on calm days. The big problem I see on my present boat is it's just about impossible to get back on board. The boarding ladder hooks to the side of the hull, not the stern.
I need to figure out a way to get back on.