I ran into what I'm quite sure is a bug, since it happens in the JUCE demo app as well as my own application.
In the demo app, go to the "Tabs & Widgets" demo, and set the Look-and-feel menu to "Use Native Menu Bar". Now try selecting back and forth between "Use LookAndFeel_V1" and "Use LookAndFeel_V2". The check mark or tick on those items will never change.
Now, if you're not using a native Mac menu bar, the tick mark will change based on which look and feel you have selected.
The way I understand it, ApplicationCommandTarget::getCommandInfo will get called multiple times, and that is your opportunity to change tick marks, alter the text of a command/menu item, etc. That all seems to work if you use a JUCE menu bar, but not if you're using a native menu bar.
Is there something else I need to do to "kick" the native menu bar into updating itself, or is this just a bug that needs to be fixed? If there is something I need to do, then the demo app needs to do it as well.