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

1. Where do you live?
2. If you live near a marina that has racing, they are always needing people to crew.
2a. Crew on a racer's sailboat and learn.

3. You can get lessons, depending on where you live you can get certifications.
US Sailing Certifications

4. Look at the Moorings and charter a boat with a captain to see if you like it. BVIs would be my first choice if you have never been. Moorings Yacht Charters

5. Boat slips pricing increases after a 40 foot boat slip. That is why the 38-39 foot boat is super popular.

6. Smaller boats are harder to sail than a larger boat. (IMO). If lyou learn on a 25 footer, you will be able to sail a larger boat with no problem. (IMO).

7. Single handing a boat is hard and dangerous. You will need someone to go out with you every time.

If you ask more questions, I will try and answer them.

EDIT:
Costs:
1. Marina. Unless you get one you can trailer. Count on $200 - $400 month depending on where and how big your boat is.
2. You will need a bottom job every couple of years for your boat. Count on at least $1,000 for this. It has to be pulled out and put on the hard.
3. Fuel is going to depend on how much you sail vs. "motor sail". People will run Galveston Bay ship channel to get out to the Gulf under power. Your boat could be way back in a channel and you have to motor for 45 minutes to get into a bay, ocean, or gulf. The further in you are the cheaper the boat slip usually.
4. Insurance. Depends on the boat.
5. Get Boat US insurance. Ours is $120ish per year.
6. Maintenance will be TEAK, I would avoid teak decks.
7. Maintenance items on Generators, Diesel engine, HVAC, all vary. A marine inspection can give you a good idea on what needs to be replaced.
8. If the Chain Plates and rigging are bad, I would move on and look at another used boat. Same with the stuffing box (although not terrible if there aren't other issues.)
9. Electrical issues can be easy to fix. Depends on the hull and how easy it is to run wires.

Look at Yachtworld and search different boats.
Island Packets, Beneteau, Catalina, Jeneau, and NEW Hunters to name a few. I would avoid a canoe stern even though a Hans Christian looks awesome.
A center cockpit will have a large berth in the stern.
Sugar Scoops are really popular and I would consider a must if you are going to snorkel or dive a lot.