My wife and I retired and got bored. We took a sailing class in Florida to learn how to operate a sailboat. Then we took an advanced class. After a few months of classes for all things sailing, we even took navigation classes on how to use a sextant. We learned how to pilot different types of sailboats. After renting a couple of boats for some intracoastal waterway trips, we decided to take an offshore voyage to some Caribbean islands. Then we started looking at used sailboats for sale to own our own vessel.
We took our journey into sailing slow. A lot of people just buy a boat and do not know what to do with it. If you are a casual sailor who is sailing protected waters, it is not really a big deal what you get. If you want to be able to travel around the world, you need a sailboat made for the bluewater trips across the many oceans and seas of the world. You could encounter high waves or even icebergs depending on where you are sailing. I do admit that real sailing keeps you fit. You need to be able to move quickly and work your muscles. Sure, there are gadgets for hoisting and lowering sails, but you need to be able to do it manually if something fails. Some boats do not have all the fancy gadgetry, but you should have modern navs and comms.
We have an advanced radar system on our boat. We also use satellite navigation and communication, but we can chart a course using our paper charts if needed. That is one of the benefits of taking our advanced sailing and ocean navigation classes. We have actually learned enough to become commercial operators of sailboats. That is pretty cool for an old retired couple who never sailed before.