A cross-disciplinary study between the two research areas of Audio Technology and Music Education was performed to assess how different aspects of education and experience may influence the experience of music listening given a typical streaming service-Spotify.(1) The point of departure is that streamed media facilitates a plenitude of versions of the same song. The paper focuses on the differences that these different songs yield from various mastering processes and production choices motivated by the end distribution media and user settings in the playback system that aim to alter the sound. These variations may all lead to differences in musical dynamics and timbre. A listening test was conducted to examine listeners’ preferences, the assessed audio quality, and subjects’ reports on how the music content affected them when given the possibility to compare versions in a controlled environment. The test subjects (n = 76) represented populations with various educational backgrounds and experience within music and audio technology. Among the results, it was found that education and experience in some cases do affect preferences.