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I've only purchased one kayak and it was used. One of the things that I looked for was how they had been storing the kayak when not in use. Any time I see an ad where the kayak is laying on the ground in the seller's side yard I take it as a red flag. Kayaks are pretty durable and for all I know where the yak is photographed is not where it's stored, but a lot of times you can just tell.
I kinda recall that Hobies beyond a certain age are more likely to have developed leaks around the drives, but I really don't know much about all that.
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