yeah, possible. or just some other MS weirdness.
Well, as I was preparing this message I was able to stumble myself into an Apple Script solution that works perfectly.
activate application "Microsoft Outlook"
tell application "System Events"
tell process "Microsoft Outlook"
-- insert GUI Scripting statements here:
tell menu button 4 of group 3 of scroll area 1 of tab group 1 of window 1 to perform action "AXShowMenu"
click radio button 69 of group 1 of group 1 of window 1
end tell
end tell
The Radio Button # corresponds to the location in the pop-up and I think they don't change much.
I'm going to post this separate for anyone looking to do what I've done.
Posted here: Keyboard Maestro 8.2.2 “MS Outlook Color Text Blue” Macro