If I were you, I would spend my money in getting a proper training from a certified sailing school, get your ASA 101, 102, 103 up to 105 course done. At the same time, volunteer as a crew from any captain who is willing to take you, be humble, work like a dog and learn as much you can. Joining a sailing club is a good way too......etc. By then, if you want to get your own boat you are ready mentally and physically.
There are many ways to get about doing what you want, but this is my way. YMMV. Good luck.
I read, I think, and I act independently; I don't come here to win a popular contest on Sailnet, nor I am here for hookup. I come here to learn, be challenged and be inspired in the art of sailing the big Ponds. I am NOT afraid of drowning in the sea, but I am afraid of dying in a nursing home and burdening those who I love.
I am old school. Integrity is to do the right thing even when no one is watching.