The only thing I can think of is that maybe VA's presses are happening too quickly for OBS to pick it up. Not typical for a Windows app...
SOLVED: The timing was too fast and I did not have to "spread" out all the key presses.
Default timing was 0.02 for the keypress which was fine for the Focused window, but not enough to get passed through to the Unfocused window.
A timing of 0.05 was enough for the command to get "passed through" to the unfocused OBS.
This brings up an interesting feature in VA then ...
Having control to send commands to just the focused window and not any other windows "listening" is kinda neat if anyone ever wanted to use that for some reason.
Thanks for the suggestions and help. I'm so glad this was figured out!