I believe we attempted something like this before, and it was only with the 'god/player damage' toggles.
That was difficult enough to figure out when looking at the interface.
Trust me. It's not pretty.
As for the coding, Megiddo is right. We try to keep it simple.
The way we have it now, no dynamic menu update is necessary. This would/could greatly complicate the code.
With the way you're suggesting, an update would need to be done for each individual client.