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As I'm slowly trying to replace the Creative Soundblaster Wireless with the Apple Airport Express, one feature that the Creative software did well was random playlist generation. iTunes has that feature too but it works in a sufficiently different way as to be frustrating.
Let me explain: on the Creative, I created a randomized playlist of 50 songs. Every time I chose the playlist, that 50 song lineup changed. On iTunes however (limit to 50 items, selected by "random") that list was static. No matter how often you selected the list, it always came up with exactly the same 50 "randomly" chosen songs. This didn't seem terribly random to me so I was annoyed and went looking for a solution.
As you can imagine, the answer was straight forward and irritatingly logical. From the solution as recommended by user snowdog99 at iLounge:
You have to include a condition that changes, something like "Last played is not in the last n days" - where n is a number of your choice. Without that, once the random songs have been selected there is no reason to change them.
And that was the sole modification. I added a further condition that the music couldn't have been played in the last day and now the list is fresh each time I use it.
"Think Different" indeed...