Re: Small affordable sailboats with ample storage? (planning to live aboard)
Its always hard to predict what boats will be available when any one person is looking ain any specific area of the world. If I were in your shoes, (looking for a $3,000 boat, in Illinois, to live on and weekend cruise), I would put together a list of boats which were a good mix of spaciousness and sailing ability. I would not worry as much about being trailerable or whether it had an outboard. My list would include boats like the Morgan 24/25, C&C 24 or 25, Cal 25, C&C Redline 25, Viking 25, Dolphin 24, Beneteau 25 SK, Pearson Lark 24, Paceship (AKA PSY or AMC) 23 or 26, and maybe a Grampian 26, Whitby 25 (AKA Continental 25/ Walton 25) or Lindenberg 26.
Any of these in decent shape and in your price range would be good boats for your purpose.
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay and part-time purveyor of marine supplies