Gotta tend to agree with Thurmond on this one...
While this is all MORE than entertaining to watch unfold, and with particularly impressive speed in terms of the metamorphosis of the project as a whole, I too think that you may be off on quite the tangent here by overthinking the problem.
This many gears, belts, what have you, are going to lead to astronomical losses from wind to genny that just won't be practical to try and make up.
Now don't get me wrong, I'm one of those people who will do something (or at least fail miserably in trying) just to prove (or try to prove) someone wrong when they tell me it can't be done. Hopefully, this doesn't turn into one of those scenarios...
I won't sit here and say that this won't (or more accurately can't) work, but will say that its probably just not practical to use such radical methods to increase alternator speeds.
What comes to mind for me is that there's a reason the typical HAWT design on here doesn't involve a transmission of any kind - efficiency. With maintenance being a strong second. Doesn't mean it doesn't happen; Chris Olson has at least one successful geared machine in the air (just off the top of my head)...
I think for your situation though, you'd be better off using angular velocity directly (pronounced "bigger diameter alternator") and then you would have all the gains of the magnets passing the coils faster, with none of the losses associated with transmissions. You can get away with this where the HAWT crowd can't, because VAWT designs need not be as concerned about large alternator disks shrouding the turbines from the wind. There may be other considerations, but blocking the blades is not one of them.
Of course, a larger diameter genny would probably cost more (more magnets, etc), but something tells me that money isn't really one of the more important considerations in all of this... Look at all those toys!
Just a thought, take it or leave it. Either way, keep us informed. One way or another, regardless of the ultimate outcome, this is good stuff, and I'm sure there is something in these 20 some odd pages for just about anyone who stumbles across this!
Steve