While trailerables are far less expensive, especially if you have place you can store them on the trailer that is convenient and free... you will find that if you keep the boat in the water, you will find sailing far more enjoyable, and find yourself doing more sailing. If it takes you two hours to get the boat in the water and rigged, and almost that long to get the boat out and unrigged... you have spend four hours each time you go sailing in prep work... if the boat is rigged and in the water... you can usually get out sailing in under 30 minutes, and the same when you get back.
It depends on your financial situation as well as your time requirements. With a boat at a slip or a mooring (which is usually a good deal cheaper than a slip, but far less convenient) you can opt to go sailing on a free afternoon or morning... with a boat on a trailer, that is usually a non-starter.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.