Join Date: Mar 2007
Location: Rouge Island
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O'day are nice little boats in that range, 22' or Catalina 25' or 27'. Catalina's in the range have a good size cockpit, and the companion way is a wide V. In that price range you'll be looking at a tiller, which is a plus and a minus. Plus, there's more room in the cockpit at achor or dock with the till up and stored, minus is you need space to swing the tiller under sail and tacking or jibing.
As for single handing, roller furling, in that size of boat you're looking at another $800-$1,200. Then there's the main, to hoist, you can run the main sheet over the cabinhouse to the cockpit and terminate at a cam cleet easy enough.