> And the answer is that different people prefer different things.

Exactly. There is no winning here.

When I was in college, I built a system for the college radio station that plays music while there are no DJs on the air. What I enjoyed most is keeping track of what songs played when (which we needed to do anyway for FCC compliance) so that we never play the same song twice until every song was played. This "felt" more random even though it wasn't.

Some people didn't like it. They wanted to hear a smaller subset of songs more often (the equivalent of putting a playlist on random). We solved that by letting users request songs through the website.

I wonder if there's a way to solve this by adding a setting called "repetitiveness". It's a value between 1 and 100. 1 is the least repetitive "play all songs once before repeating any" and 100 is "play the same sequence of songs every time."