So I've been playing around with triggering nightmode remotely via a shell command:

#!/bin/sh
echo '<event type="NightMode" value="on" comment=""/>' > /tmp/flashplayer.event
/usr/bin/chumbyflashplayer.x -F1

I've found an interesting case, might be able to call it a bug, the behavior is different then might be expected.

If you are in the control panel and have music playing, then when you leave the control panel, by pressing the sleep button you are prompted with a screen giving you the option to set a turn music off timer.  This is a nice feature for direct touchscreen operation, unfortunately the shell triggering of nightmode didn't keep up.

If you send the remote command when in the control panel with music playing you will also be prompted with this screen, and there doesn't seem to be a shell way to get past it.

I imagine a workaround of turning music off first then entering nightmode would probably work, but then you have no music.