Jay you raise some great thoughts.
Getting ready to retire is a great time to identify the things you would like and then do them.
I moved from camping in a 15ft Trailer yacht to sailing a 35ft boat. I had looked at a 50-foot boat filled with plenty of features. But when I picked up the sail bag, I realized that my sailing solo days would be limited.
You need a boat that you can master if solo sailing (or sailing the boat with non-sailing guests) is in your future. 35-36 ft with a traditional hull and designed to manage a turbulent sea will make sailing in all conditions manageable, if not enjoyable. Choose a sail plan that you can handle. Smaller sails are better than one great big sail. Note Mast head sloops are jib priority sized. A Bermude rigged boat leans to large mainsails and smaller fractional jibs. A cutter rig is very versatile in sail plan.
Make a list. Certainly, a shower would be nice. I have on that is in the head. It uses a shower curtain to curtail the water. It is not an easy functional experience. It is not used. Shore showers are the norm. I am looking into a cockpit shower. Don't look if we are in the same anchorage.
You could use AC in the Chesapeake Bay. You would need to have heat if sailing year-round is desired. Heat is also nice in the shoulder sailing periods of early spring and late fall.
You know what you liked for the past 20 years. Incorporate those thoughts into a list of boat priorities. Then match boats to your list. Whatever you choose will be a compromise of important and doable features.