I grew up sailing in yacht clubs on sunfish, Pixel, and crewed larger boats. Never owned my own boat, always borrowed. Can somebody learn me on what it takes to own a sailboat? Or point me to some forum where I can ask these questions? I would either trailer it from home each time or find a place where I can store it. I have no idea of the ballpark cost of registration/storage/fees. I am in New York.

Looking at Hobies between 14 and 17, small enough to solo. ~$3000 for a boat with no major issues seems reasonable.

Example:
https://longisland.craigslist.org/boa/d/brightwaters-hobie-16/7585382463.html