I would suggest you focus on a trailerable sailboat that is truly fun to sail. Presume that anything trailerable results in camping aboard, not
living aboard.
Something that works in your favor is that trailerable boats tend to remain in far better condition than boats kept in
marinas, so you can consider 30+ year old boats. They can be hard to find, you may need to go to a bunch of yacht clubs in your area and find "for sale" signs in the dry
storage yards.
$40K is probably barely enough to consider a Farrier
trimaran. These are very fun, very fast, roomy, great for
day sailing, and probably the easiest to go from highway to sailing of any trailerable sailboats, and that includes sailing dinghys. Unlike
keel boats, Farrier trimarans are easily launched at a normal
ramp. If you can find an F-25C that is in good condition, that would be the ticket. Really high quality, but since they were kit boats, the finish on some is annoying. The F-82 is the new version, and I know of one
for sale, I don't know the cost (contact Sam
samjwhitmore@hotmail.com or (321)363-7613 in Orlando FL).
But you might be happier using a lot less of that $40K for the
purchase, and then being able to act like a rich man when owning the boat (because every boat likes to vacuum all available
money out of your bank accounts). Here are some far cheaper, but still FUN boats:
If you want to day sail more than overnight, I would suggest an Etchells or a Soling. You can pick them up for on the order of $5K. Simple, lots of
cheap used good
sails available.
Cheap gear if something breaks. Really fun to sail, and easy to trailer (you need a yacht club hoist, generally not much of a problem but you need to be a YC member).
If you want to
cruise more than an Etchells or Soling will let you, then I suggest a
racing trailerable
monohull like an Olson 30,
Santa Cruz 27, Express 27, B32, Hobie 33, CF 27, an ex-MORC boat, maybe even a Melges 30 or a Mumm 30. Take a look at the sailing anarchy classifieds for some examples. Note that some of these might require permits for trailering because of beam exceeding 8.5 feet.
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