When attempting to trigger such macros within a Comment action, the behavior is not necessarily repeatable. That is, it's not always the third attempt that fails.
Such macros seem to always trigger when using other applications that accept text (e.g., TextEdit).
I'm currently using: Keyboard Maestro 10.2, Sonoma beta 14.1 (23B5067a)/MacBookPro16,1; however, I've seen this anomaly with Ventura and other older version of macOS.
Curious, anyone else seeing this? @peternlewis, might you have some insight on this behavior?
Sure - because making a change to your macros is one of the things that resets the Typed String buffer.
So it'll only work if you can do it fast enough before Keyboard Maestro does a save in the middle of the characters. Generally I'd expect if you pauses for a few seconds for Keyboard Maestro to save, and then typed it quickly, that would get through. What you are seeing is the result of the save that is happening while you are typing because of the previous changes.