Comment 11 for bug 1828595

Yes, issue is __import__ does not reimport a module if it is already in namespace.
Potential solution would be to first del(ModuleName) and then __import__() but I have not tested it.

An example of a complex plugin to test is attached. Make sure you drop the whole folder in plugin dir.
You can edit the message of the popup and see that it does not get picked up by kicad without full restart.