It looks like trying to compile the source for the Generic HID program is a pain on windows so I might give it a try on a Debian/Ubuntu VM later.
I had a chance last weekend to almost everything up. I managed to wiring everything up (except the shield ground) while doing the crappiest soldering job I have ever done since I could not find my helping hands. I might end up redoing the wiring. This weekend I plan on placing everything into the enclosure.
Sokol1, I thought about using an external ADC such as this from SparkFun
https://www.sparkfun.com/products/9056. I would actually be curious to make a shield or something that would allow you to plug in any DB15 joystick and assign each pin using jumpers whether or not it was ground, power, or data. I am actually surprised nothing like that exists on the market.