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So my question is what boats maintain their values the best? All thats on my radar right now are Island Packets and Cheoy Lees.
Well of those two I would say Island Packet, yes they do a pretty good job of maintaining value, Cheoy Lee, not so much. Lots of Teak decks and they can be hard to sell, let alone maintain with all that bright work. Of the "lower price" boats Catalina seems to hold it's value as they are known for excellent support even on older boats. As does Saber, and Canadian Sail Craft. But I would not worry about resale, just find a boat you like. If you are thinking get a boat to learn on then move up, then I would have to suggest Catalina. They are a reasonably well made boat and when in good shape and with a reasonable price they seem to sell very quickly. Selling quickly is far more important than resale price. Storage and insurance can eat up a higher selling price quite quickly!
 
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