If I tag a playlist as "Always Randomize Contents" and "Automatically Repeat", when the playlist reaches the end and wraps around to the beginning, it does not re-randomize at the wrap-around point, so I get the same shuffle a second time.

Should I put that in the internal bug list?

Or should it work like Winamp where it just keeps randomly playing tracks, not careing if the song has been played 2 playlist positions ago....?

Should I put that in the internal bug list?

It's already in there.

Heh, no. Actually, I want it to work exactly like it does now, only I want it to reshuffle when the list wraps around. I have a feature-idea related to this, I'm holding off on discussing it until the pieces are in place.

Bug or feature?

As it stands, at least you know you won't get the same child tune/playlist twice in a row (last in one shuffle and first in the next, IYSWIM).

That's what Least Recently Played is for (when it works). My usage for this feature would be different.