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i have noticed it before, but new years it was painful. the randomize algorithm is a bat glitchy. i had the same song play twice in a row 4 different times (differnt songs each time, but played again back to back).
if i click on another song to not play it again, the algorithm appears to reset and start over playing songs it already played.

a solution

like windows media player, instead of the "random" checkbox, have the algorithm physically shuffle the list.

1) it is the same songs in a random play order so the same song can not be played twice unless it is in the list twice.

2) it will allow the host to see what song is coming up and make changes to the order if necessary

3) moving songs will not confuse the algorithm and so they will play as the host expects

4) allows for an extended break should the need arise (party needs a few dance songs, slow night of singers, recovering from ballad hell, etc) and the host being in control of it.

I'm also encountering the randomized or lack there of problem too. It came to a point that I no longer use the randomize feature and I will manually shuffle songs if my fillin has more than one song from the same artist. This technique will always show me what fillin song will play next. But, I second your suggestions for enhancing the fillin playlist feature. I hope Piotr can add it to KP, although I haven't heard anything from him for a while now. I'm hoping he's just taking a holiday break and will be back soon.