Buying a 1st boat
The only way you will learn to sail is to do it. The only way you will do it is if you have some experience.
Take an ASA or US Sail keel boat sailing class. Learn the basics.
Buy yourself a boat you will be comfortable with, and sail it. While you''re sailing it read everything you can get your hands on. It will make more sense if you can read and experience it at the same time. My first boat was a 28 footer, my wife wanted something she felt secure in and was self righting. We did not know a thing about sailing except we had chartered with a couple for a week in Lake Erie and loved it. We learned as we sailed. My second boat was a 25"11 foot racing boat. My present boat is the boat of our dreams a Morgan 384. In the middle we took sailing classes in flying Scots, and ASA classes in 40 footers. We took navigation classes, bisic coastal cruising classes. We learned in all of them. These classes are arranged to take you in steps as your experence grows.
But you need the experence. One of the most
frustrating things I experienced in one of my advanced classes was with a gentlemen who read extensively about sailing but had never experienced it. He had never been in charge of any size boat himself. Everything he did he related to "well the book says..." or "is this what the book ment by..." Very unnerving for a few on board offshore some 100 miles.
If your going to retire in four years I would assume your not 30 something so racing is not probably something you will be into, there for it will be much harder to catch many rides with day sailors or cruisers. You need to get as much time onboard as possible. That means buy a boat regardless of what it is. Some clubs will have smaller boats you can use to learn basics but they won''t get you cruising on weekends to learn. It is easier to invite experienced sailors to sail with you than to catch a ride with no experience.
My 2 Cents..