The idea of doing the whole thing from scratch sounds appealing too, as you mentioned, and with any boat one builds there is that line between interest in the project for itself, and the desire to get out on the water.
The more I think about it, the more a fully battened rig on a mast secured to the outriggers, with multiple reef points and a roller furling headsail sounds like a great way to have my go fast cake, and eat it (be able to survive stronger winds, and maintain a balanced sail plan while I'm at it) too. Is it possible to do all of this, and keep the controls mounted to the amas of the sail rig, so I can keep my kayak a basic functional kayak?
Could I take it even farther and put the big sailing rudders on the amas themselves ala catamaran, and get good steerage without mounting a rudder on a kayak which definitely doesn't need one for itself?
Perhaps I can't, but the more I think about it, the more eager I am to try it and at very least see if I can get a great story and some experience out of it. Either way, for now, the work is building the kayak, which leaves me months and months to continue to scheme and plan about the sail rig itself. =)
The first dilemma seems to be determining how much sail to carry, and how to best carry it low to the water, while maintaining a balanced rig... hrm. I suppose for that, I'd need to know a bit more about the shape of the hull and it's dynamics in the water, right? How does one start this process of designing sails for a given hull profile? What additional information do I need to bear in mind since it's a multi-hull rig?
Would it be appropriate to experiment with self made tarp or nylon sails, if I intended to eventually get decent dacron sails, or would none of the information really cross over?