Boat Choices: Double-Check
I agree with Jeff. You have a good plan for accelerating your learning process, but there is just no substitute for time spent with your hand on the tiller and adjusting the sheets in a variety of wind conditions. You can learn the basic principles from an instructor, but, after the instructor is gone, when you are on your own, things will happen that the instructor didn''t tell you about. Sailors spend the rest of their lives learning the finer points of sail trim and helmsmanship and seamanship. If you get caught on a lee shore in heavy weather, you need to know more than the basics to keep the boat off the beach. Small sail adjustments can make a huge difference.
I see people drifting down on other boats because they don''t understand the most fundamental principles of how the rudder and keel work.
Take six months to talk to lots of sailors, boat brokers and other knowledgeable people about different types of sailboats. Ask lots of questions and let them educate you about all your options. After that, you''ll have a better base of knowledge, to help you decide what kind of boat will best suit your needs.
You''re retired, and have time to sail a small boat once or twice a week. You''re young enough that you can afford to spend a year buying and preparing your boat and yourself to do whatever you want to do. If you are over-anxious and get in over your head, it could turn your dream into a nightmare. What you are about to do is worth the time and effort to do it the right way.