Originally Posted by paul323
More advice from a guy - please forgive me....
A lady I know is in a similar position. Her strategy is to buy a smaller boat - Santana 22 - and learn all she can with it, doing all maintenance, repairs, upgrades, learning to sail solo (and with others). Make mistakes in a small, comfy environment, where the cost of mistakes - both financial and in terms of consequences - are less. She also crews on larger boats for the experience.
I did the same thing. I bought a 22' boat that I knew would at least float. It had everything I needed to learn how to sail, but I wanted to teach myself how to do fiberglass repair, hull and deck painting, bright work, rigging, etc. and not on a boat that cost a lot of money. I'm glad I did it.