WMBR does not have automation (yet). It's not that the volunteer MIT students and alums who maintain the station themselves (without any assistance from MIT itself) wouldn't know how to develop a system, it's that they haven't had time to do it yet. MIT is a high-demand school for the students, as are the careers of the alums! There is a digital music playback system partially installed, a project not yet done. It's a student/alum project that been at about that status for at least a few years.
One thing about MIT students/alums, if possible, they usually want to build and/or at least configure equipment as much as possible themselves rather than just buy stuff or purchase it even partially pre-configured, regardless of whether it takes longer. The station was originally completely built by MIT students, including with completely home-made studio boards, as a student hobby around 60 years ago (it went on the air in April, 1961). The station wasn't originally MIT's idea, students just acquired the building space for an electronics project, and when done, MIT had a radio station. Despite the community outreach and listenership it has developed, it has always since been maintained with that philosophy. That was why it was the last college station in the Boston area to finally go stereo in 1987.
I had this memory that the original MIT radio station ran a signal through the electrical system, but looking it on Wikipedia the signal ran through 'dorm wires.' Do you know what this system was?