re: Aynone here have a sail boat or know much about them?

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I assume I'd need a 25 hp outboard or so on it?

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you can put a 25HP if the bracket is big enough but you certainly wouldn't need to. Most people use <10HP or so. You only need an outboard to get out from the marina to the open water and raise sail. I got by just fine on my 22' daysailer, and it displaced 3500#, with a 6.5HP. With $10k you could get a good sized boat ready to sail that might even have an inboard.