Intermediate sailor seeks advice re: liveaboard pocket cruisers
My situation was somewhat like yours a few years ago (comparable skill level and ambitions). I bought a slightly larger (30ft) boat for slightly more money, but I think my experience may be useful.
1) I found actual formal sailing lessons (ie by a sailing school) very helpful. Even when the instructors were less than great, I learned from the other students (even from their mistakes). Also, having a much more experienced sailor around gave me confidence to try things I might not have normally tried, and also, being in an educational environment in a sense gives you permission to make mistakes- after all, you''re supposed to be learning.
2) I am an avid reader but I found that what one of my instructors called "stick time" (ie time at the tiller) to be one of the greatest teachers. I found myself deliberately curbing my reading and making sure I got out not only on my own but on other vessels to improve my skills.
3) I bought an older boat with the intention of fixing it up. I''ve enjoyed that process, but my background in light carpentry didn''t prepare me for the intensity and multiplicity of tasks incumbent in making an older vessel perform the way it could. Time spent fixing up a boat can often be time subtracted from sailing. If your first aim is improving your sailing skills and enjoying sailing, you might want to avoid a "fixer".
Good luck. It sounds like you have a good attitude.