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if you think you are going to sell in a few years, and you don't want to take a huge hit, think used and be patient.
I bought my first new boat over the winter (previous two were used), a Privateer 24 center console. I went new because I wanted something customized to make it more family friendly than a typical center console (basically, I made it into an ocean-going minivan). Also, this is my last boat, I cannot fathom wanting anything else. So I'm not worried about depreciation.
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