Well, my first thoughts for your idea would be to cosider for the commands that there is /anon on, and /anon off (I think at least, not sure). If you can use the commands like that, then I think you could easily enough make buttons that would turn /anon on, and then set the display to show *On* or whatever you'd like. And then clicking it again would /anon off, and set display to *Off*.
I'm not too sure however about the turning anon on while in roleplaying, and haveing it "detect that you are". All the buttons/status would just have to start one way until you clicked them, ect.
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