Hey Aaron,
This sort of task can be quite mystifying until you know how various aspects of Keyboard Maestro work.
As you become more familiar with KM's features figuring out how to do things gets easier.
You have to realize that you can test for a menu condition — and based on that you can branch to selecting Shuffle (ON or OFF).
NOTE — See how I'm using the path to the menu item? This is the fastest way to address it. Otherwise KM has to search for some menu item named “whatever”, and that slows things down.
-Chris
Toggle Shuffle On-Off.kmmacros (6.2 KB)