Sadly, the app indicator icon still disappears when it should not.
To be sure, you have "Stop tracking status when off" enabled, and after the server has been running a certain time with no users connected, the display switches to off, right?
To increase timeout, you could open /usr/lib/hildon-desktop/openssh-status-widget.py and in line 162 Code: if self.sshJustOff < 1: give the condition a higher value. Then restart the status menu.
if self.sshJustOff < 1: