Aloha !  I am looking for some help as I am banging my head against the wall. Set up new HTPC as described and remote work generally OK with an activity including two devices the TV and a FLIRC> HTPC>PLEX setup.  I am trying to map some key any key on the remote to the Super L key on the keyboard as this triggers the OS window switcher and allows me to move between chrome for YouTube on tv and jellyfin.  Seems a simple thing but fro the life of me I cannot.  I have tried using F13,14,15 and the little context menu key and it always sends key 108 to the FLIRC. Ok so it is static and defined only by the Skip - I guess? I try to edit any button in the Skip and get o where you can drag a circle onto a key but HOW do you tell that circle the keyboard key you want it  to emulate? It si like the Skip and the FLIRC dont play well together which is really confusing?

Pair an arbitrary button to the keyboard shortcut on the Flirc usb app.  Have you tried that?

Yes.  the issue is the keyboard on the FLIRC is limited to the standard keys and the special keys are under the Skip S1 AND when the window in focus is Chrome or Jellyfin for example you need a key that they will be ignored so it can be passed to the OS. In fact if you use the FLIRC GUI and try to select the Windows key (Super L) it requires you to press it in combination with another key - so no joy.   I will try alt tab in FLIRC maybe that works.....

Well - that doesn't work. Alt Tab can be triggered but the behavior is different and not remote friendly. 

Well I solved it!

Alt Tab did not work but widows key +a does work and it allowed me to correctly map it to the "context" button on the Skip S1!  Fantastic!

Great hardware fro sure.  That said I find programming the Skip S1 to be super confusing - I think there is a guide need especially when using in combination with the FLIRC USB. my .02 of course.