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Hi SW -- my advice (free and worth every cent) is to take a week long sailing class for day skipper certification. Sailing isn't hard but I find some people have gone so far as to purchase sailboats for the 'romance' and then realize that a) you are at the mercy of the wind to get where you want when you want and b) there is a reason they call it a 'boom'! As a result of this fairly common phenomenon there are many slightly used sailboats on the market. After taking the class, charter a boat for a week - take it down the keys or over to the Bahamas. Then when the time comes to buy a boat think of your first boat as a starter - something that will get you through 2 - 3 years until you learn about all the things you like, don't like and wish you had in a boat.
You will find sailing imitates life - sailors have many opinions and ideas often very conflicting but enlightening nonetheless - in the end you choose what is right for you and sail your own course.
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