Guitar Wing issues SOLVED!
Not only does it work cool, but it looks pretty cool. And when it looks cool and works cool, I'm a whole lot happier.
After getting it working with the computer, I moved on to using my phone as the USB hub. I have an iConnectMidi1 cable (lightning to 2 x 5 pin MIDI cables) and am able to use the wing as Bluetooth MIDI with the MidiBridge app and just route it out to the iConnectMidi1 plugged into the guitar head. That makes it extremely portable.
Next step is to get it working with my bass effects now since I'm playing bass in several bands instead of guitar. In any event, I'm starting to have fun with it and am seeing more possibilities. The good news is that Line 6 is very, very consistent with their MIDI implementation, so I think all I'll need to do is move from the Flextone head to the Bass Pod Pro and it'll be done.