I did in the beginning of this year, bought a Cal 25 and now have a much nicer Oday 22. Learning how to actually sail was not very difficult for me as I have now nearly mastered my particular boat. I probably should not say "mastered" but I mean I just know the basics of it pretty well and comfortable with it even single handing which I do a lot. I have NOT mastered sailing yet, more to learn.
What I did during my first day out with it, I was solo and I motored out and back in, no sails. Next time out, I hoisted the main and sailed under that only, done well. The third time, I had a couple friends with me and I hoisted my main and genoa, all went ok. I made a few mystakes that just caused me extra work, nothing major. In time I learned to "prep" my boat before leaving the dock. By doing this, once I get out in the open water and wind and waves are kicking, I can hoist my main right away and get under sail.
I have a certain routine I now do when I single hand and I have it running smoothly doing this. I think a lot of my success in learning on my own has to go to my boat (and all the helpful people on this forum) because its just in such good condition inside out. Everything works well and its just easy to handle. I sometimes just go out and drop my anchor to watch and film the sunset. I once even had the nerve to anchor, put my swim ladder down and go swimming. No big deal but seems kind of crazy when you do it solo. It was a calm pretty day though and I was able to go around my hull with a spong and wipe the bottom of the hull. Oh and no, no sharks here :laugher I remember thinking, the boat looks huge when I am out of it swimming around it. Talk about scary if you can't get back aboard for some reason. Anyone ever seen open water 2? :laugher This is why just for extra safety, next time I decide to take a solo dip, I will put 2 swim ladders down just incase. Anyway, as I mention in another post, it is learning how to do general maintenance, fixing, or working on the boat that was and still is difficult for me. I am going to get a manual for this that I heard was really good. At last, been there, done that and doing well so far. Hopefully I will be taking my first mini cruise this October which will be a big step for me.