Could be possible that Winamp follow a sort of rules for the random play?
I mean... I've got a lot of mp3, with a lot of different genre.
Obviously, when I play them randomly, I pass from metal to classical to metal again.
Why can't set to follow the BPM and look for the next song to play with a number of BPM near to the last song's one?
I hope you understand what I wrote...