My overlay won't rotate at all

Here there is no valid command (no “shifts to” or “scales to”) and the coordinates are wrong, since you’re using the scale and x y in the same line like you would for a character, not an overlay with the exception of adding to the background. :see_no_evil:

You’ve also done it here:

I’d change it to:
@overlay EXT. ROOFTOP BAR CHAIR ONE Z1 - NIGHT scales to 1.720 1.720

@overlay EXT. ROOFTOP BAR CHAIR ONE Z1 - NIGHT shifts to 170 7 in zone 2

You can follow the same format for the second one too. The scale and shifting need to be separate commands.