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I've thought of this before. If you get a swing keel or wing keel I bet this could happen with a stepped mast. I was looking into a O'Day 322 to do this exact idea you are thinking of. I was going to sail in the Long Island sound area of CT but if the itch was there I would love to drive it down south and explore.
"estopa" - [est'opa] is portuguese for Oakum.
1986 Oday 222 #686