Believe it or not, WDBK programmed a mainstream alternative format between the demise of Y-100 and the startup of WRFF, around the time it started encoding for PPM, and it actually showed up in the first PPM ahead of several higher powered noncomms and regional AMs. That success was shortlived due to the aforementioned college administration (they opted to limit access to the building to weekdays, automating other dayparts and effectively killing much of the station's momentum and student enthusiasm). The college wasn't interested in funding streaming at that time (2003-7 timeframe). I suspect the college set up the stream in 2014 only as a bone to the students in exchange for selling their FM.
The article alludes to CCC wanting to sell the station rather than repair its infrastructure (in this case, the antenna tower, which by 2014 had been in disrepair for over 15 years), probably one of the reasons the station didn't ultimately sell.