The Hobie looks pretty cool. I still think I want to try to build my own small wooden vessel, but that's definitely a neat setup, and something I can look to for ideas.
I think I may need to get over the idea that I can have a kayak that's also a racing dingy, and look at less powerful rigs like the Pacific Action, or WindPaddle. They don't go to windward, and apparently, while the PA will do 90 degrees to the wind, everyone seems to agree that by the time you're 90 degrees off with no leeboard in the water, you're already losing so much sideways, and slow enough, that, well, paddling works better.
Both of those look like neat ideas, but looking at a device which requires bungies and multiple lines on the deck, and a defacto spring loaded caning device
without the speed provided by a larger sail, nor the stability of amas kinda scares me, but this might just be my imagination. I'll head down to their local dealer (still 300 miles away, but I think that's worth it, given that I'm going to be spending a few hundred hours building my boat anyway
) and see what I can dig up to most assuage my fears and see how it would fit the kayaks I'm looking at (I hear a very narrow deck might be problematic)
The main advantage of the BOSS system seems to be that it is theoretically stowable, and something which can be set or struck from on the water. (although the zipper reefing idea is pretty neat) I'm not sure if that bit is important to me, given the local waters, and my plans, but the reefing part certainly is. I'm a little curious about their decision to make a tall sail for a kayak, given the high center of force should theoretically make it a lot more "tippy", but no one in the videos seemed to be having much of a problem. It's a shame it looks so "utilitarian" but it seems to have quite the track record.
I had to deal with the design issue when testing kayaks. They make a kit which does sail very well apparently, with the clc sail rig, but as a kayak itself, it's not nearly as fast, maneuverable, or just plain fun, as the kayaks I fell in love with which were just designed to be plain old kayaks.
My biggest fear with the CLC is that it slips over the mast, so there is no means of reefing or dropping sail at sea. That just really isn't ok for the area I'm looking at crossing. All the other benefits; pointing, more sail, etc, were just things I thought I might be able to eak out while modifying the rig into something I could raise, lower, and reef while underway.
Thank you both again for your thoughts and information. I'll try to visit some places and get a chance to get my hands on some of this gear and try it out. =)