Jake - Yeah, actually, the sail will not slide down nor move up without a pretty good amount of force on it. I am starting to think this may be the root of my issues though. I can pull it down by hand, I just use the downhaul line to do so. I think it may be time to try to agressively clean the luff and perhaps check the rope for shrinkage - if the luff rope has shrunk too much, I can see the tape bunching up in such a way that it is "thicker" than will move easily in the mast. I may resolve my issues altogether by getting the sail to move smoothly and easily in the track. I'll search the forum archives for threads on sail cleaning and luff rope shrinkage.
DaveW - I am going to run the sail up the mast to see where things are tight, and to see that I've got the correct clearances on things. The hook is off to one side slightly already, but I will consider bending it, and check that the offset in the aussie ring tilts the ring the right way to help move away from the hood when the mast is rotated.
GeoffS - Heh, yeah, I grew up here, but didn't go to St. Anne's, but went to VES and then UVa. I live in the neighborhood between St. Anne's and UVa. There really isn't anywhere here, but the Chesapeake Bay is only a two hour drive which I don't mind. I will try your suggestion on the boom. Thanks!