I have a habit of listening to a single song over and over again. I am able to do so for about 3 hours. Using such randomizer technology, this time will be dramatically prolonged...
As someone that does the same I think it's to do with "ignoring" the music. I can listen to the same song for ~3 days at a time (and the same artist for longer, up to a week) but I will often find myself not realising I have music on or be sitting in silence and not notice.
For example from October 20th to October 22nd I listened to Kanye West 200 times in a row and I've listened to "Bob Dylan – All Along The Watchtower" 717 times in total. Music directly reflects my mood so if I'm happy for 6 hours and find a song that I find to be happy then I have no problem with it on for that entire time.