Aloha and welcome aboard!
Yes, lessons will help you with anything uncontrolled.
My personal feeling is that it's best to find a boat which suits your sailing needs for now (not the future) and pick something that is common to your area. You'll have a better chance of resale if you don't fall in love with something which is highly modified or an odd duck.
Good luck with whatever you choose. If you were on the west coast
of the US I'd recommend a Catalina
25, 27 or 30 but they may not be as common where you are.