Re: A bluewater live-aboard for under $20k
Look around for a freedom yachts cat ketch or and an offshore 33 cat ketch. both have self tending sails and full keels. You're doing it wrong if you to put your beverage down to tack. The biggest issue people have with them is that they just look wrong with free standig masts and no shrouds or stays.
Experience teaches us things we would rather not know.
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S/V Shakti '81 Offshore Cat Ketch 33'