Razer Deathstalker Keyboard. Win-Key no longer recognized.

I have been using a Razer Deathstalker keyboard since about 2010 on multiple computers and it's been working fine. The only issue I have had with it until now is that the windows key (option for osx), wont allow me to use bootcamp so you have to keep a second apple keyboard plugged in just for that option key during boot. I mention it because that may help isolate my bigger problem now.

I just trade my old razer mouse out (death adder), for a new one "Naga Trinity". In doing this I also removed the second apple keyboard and then installed Razer Synapse 1.82.35.

NOTE: I originally installed USB overdrive until I realized the Razer Synapse app worked on OSX. So, I uninstalled USB overdrive right after installing, then installed Razer Synapse. I may well have messed up something in this phase, but until now I haven't found it.

The main problem: my windows-key will not work at all on the Deathstalker Keyboard.

I can change the modifier keys in keyboard prefs and it seems that the main issue is that the windows key is simply not recognized.

Additionally, the keys on the side of the Naga Trinity seem to not work after programming them in either (photoshop & chrome).

Here's some pictures of the settings I'm at too.

I'm having a hard time isolating the cause of the "Windows key" no longer being recognized as 'option', or anything else. Any help?

I really hope that Razer and Apple can work together better as Apple enters the VR/AR space.