Re: who knows about sailing and sailboats?
I wouldn't buy anything as big as a J-24 for your first boat. If you're content with having a daysailer with no cabin, you should be able to score a good used Etchell or Lighting or many other ~20 foot boats for only a few thousand dollars. I just bought a Lighting for only $1100 with the trailer included. Granted it's not in the best shape, but just buy something cheap to get your feet wet with. None of the one designs are going to depreciate much (if at all.)
And don't buy anything with a wooden hull.
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