The boat is not noted as being too pleasant a sailing craft, as Wooden Boat magazine and CLC have stated. However, no kayak is particularly good at sailing. You need a deep weighted keel for performance sailing. That or a wide beam. Something a kayak clearly lacks. So they all heel over easily and excessively, and tend to skid. Do not expect the boat to go sailing up into the wind or to work like a "normal" sailboat will, for it cannot.

Your bow height sounds odd. Especially since you say you have tried scooting forward and have been unable to lower the bow into the water. I have a MillCreek 13, and it is quite sensitive to where I sit in the cockpit. At the farthest back, my bow barely comes out of the water. So I find myself wondering if you built excessive rocker into yours through improperly cutting the panels, particularly at the bow.

The outrigger is a viable option if you are heartset on sailing.