Hello there.

Although there are 400+ tracks on the server space, the 48hr period shows that 250 tracks played in total with only 66 unique played. This means that only 66 of them repeated for about 4 times each, leaving the rest 330+ un-played and sitting idle. Why is this? Isn't AutoDJ supposed to play random and more spread out the songs of the playlist?

You've got a connection problem between your autoDJ and the web interface.  The failsafe playlist (used for exactly this situation) contains precisely 250 tracks selected at random from your general rotation playlists, which exactly matches what you described.  Check your nextsong.log for the error details and if you still can't figure it out, open a ticket with the helpdesk and our staff will be happy to help.