Ok. well restarted.
So yeah, in Notepad, when I direct the command to be placed there, I can do the SHIFT + W, hold it down and get this result:
W*WWWWWWWWWWWWWWWWWWWWWW (so it's doing the * and continuing the sending of W)
But when I switch to the game, it won't do it. It'll only kick it off if I wildly spam on and off the SHIFT + W keypress
It behaves like that SHIFT KEY is blocking the ability for the next key (numpad *) being sent or recognized.
So if I choose just the W key, then things work ok in the game and the numpad * is passed normally.
When I do SHIFT+W instead, it won't work.
Additional information, this is a TrackIR reentering key bind command (numpad *)
I did try to EXPLICITELY send the resulting numpad * to the TrackIR application also running, but that made no difference. As it stands now, with just the W key being used, there is no specification to send the numpad * key to the game nor active window. The 'Send Command to this target' is unchecked and it works with just W.
But again, when I try to do SHIFT+W, then it doesn't behave.