Since my origonal post was a little while ago, I figured I'd make a second instead of just editing.
Got JoyToKey working --
http://www.electracode.com/4/joy2key...%20Version.htm -- it's a program that allows joystick input into applications that normally wouldn't be set up for them. This way Ventrillo can use a controller button as a hotkey.
Just by having vents hotkey as one button, and matching JoyToKey to that button, DOES NOT WORK. Once you have JoyToKey set up like you want, go back into Ventrillo's setup and remap the hotkey to the controller's version of it -- it reads differently this way and works just fine.
I'm using a set of drivers called XBCD. They are a little tricksey, and don't install like normal drivers, so if you have any questions just ask. The guide I followed for them is here:
http://xbcd360guide.50webs.com/
Rumble works but its annoying!
The 3rd downloadable config file makes the L/R rudders work as digital buttons.
Vent works with JoyToKey.
Only thing left is the Xbox Live button, which I think they are working on in these drivers.
I also read that microsoft is planning to release a USB dongle to allow their wireless controllers to work. I may switch over then, dunno, I hear the wireless controllers are actually a bit unnaturally heavy.