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There is some good advice here. I have been sailing since 16 (Hobie cats). Bought my first mono hull at 21 (Watkins 26') and have owned many boats since then. I am now 38 and currently living in the Bahamas. I now own a Morgan 41 Out Island.(Not the most beautiful boat but GREAT for a family in the Bahamas; shallow draft, two full heads, two true sleeping cabins, wide and stable, etc., etc.) I don't think you need to go overboard on your first boat. Get a good trailer sailer and keep it at your house or a storage lot. Many good models in the 20 -25' range. Smaller boats teach you how to handle a boat quicker because they react quicker to changes in wind/current. They cost less to outfit and maintain.(A main sail for a 24 footer is about $500 one for a 41 footer starts at $3000 and goes up from there) They are easier to sell if you decide sailing is not for you or want to buy a bigger boat.
Sailing is a great way to be busy doing nothing. I love it and agree that it is more a lifestyle than a hobby. Start slow and see where it takes you.
good luck,
Ben
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1986 3.2 Carrera
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