re: Any OBers into sailing, own/sail your own boat?

I spent a few years working for a company out of St. Petersburg FL; Sailing Florida.
They have everything from 22’ up to 50’ monohull or catamaran. We did sailing lessons (aimed more towards the cruising crowd), had rentals, sleep aboards. You can do basically all the classes for ASA to get you confident behind the wheel, they also let you sleep on the boat while you do your classes. I’m sure there may be something closer to home, but definitely worth checking out; I think they’re up to 30 different boats.
I’d suggest shopping around and testing different boats by renting them. Some of our customers came into it thinking they this, but wound up with that. You may also not enjoy blue water sailing and would rather hop from port to port.