Re: asa school vs buying own 20-30ft and teach self?
Benjamen has a point. I seem to be in the minority, but I highly recommend taking the course first. For starters, you will become a better sailor quicker. Secondly, the price of the boat is just the beginning of the expense. You have to add in everything else from dockage to maintenance. Lastly, you may want a totally different boat after lessons than you thought you did before.
I started with an intro to sailing course on the bay in Miami and have since completed ASA 101, 103 and 104. I learned something valuable in each and every one. I also like the suggestion of going down to the caribbean to take your lessons. That way you make an exciting trip of it and you'll be prepared for all kinds of sailing when you're done.