I kept at this - figured out 2 problems that I think are causing the hard crashes/BSOD.
1) If the headset isn't picked up by the sensors, crash
2) I had a crazy problem with my CH Pro Pedals - I would touch them and they would deflect full right and not work. I believe this was also causing a crash of FlyInside. I was able to fix by going into the Calibrate... in FSX and resetting the CH Pro Pedals using the "Default" button which is like a reset.
After that I was able to fly the learjet although that crashed shortly into the flight, same with the default King Air 350. Again, I'm 99% sure these are related to my sensor placement. The Vive is setup as Full Room so when I'm sitting at my desk it's not the same as if I was in the middle of the defined play area.
I did get a video recorded of my in the Piper Cub w/ FlyInside. Check it out!
https://www.youtube.com/watch?v=T4BQwBKts9k