Re: asa school vs buying own 20-30ft and teach self?
I took a basic sailing course for a summer at the local yacht club when i was 12 and sailed thru my teens. Then joined the military and never sailed again for 20 years.
5 years ago i took what i would call a refresher course for a week. One on one with a ASA instructor and received my basic, keel and bareboat certs. Yes; it was expensive, but, it was worth every penny.
i am absolutely amazed how much more i know than than a lot of other sailors. Docking, anchoring, systems, maintenance, and sailing in general.
But ! You can learn a lot by joining a yacht club and sailing a small boat to learn your skills. It's really the only way to learn to feel the boat. There are a lot of cheap programs out there.
Another option would be to by the boat and hire the ASA instructor to go on your boat. it's a lot cheaper.
Or just buy a sunfish or laser; sail, sail, sail and then move up. You will lose very little money this way.