Why is it that even when on "shuffle" mode, there are still 50-100 songs in my playlist that NEVER play? I keep iTunes on for 8 hours a day at the office and for some reason it seems to play the same 200-300 songs over and over again...
iTunes doesn't really play randomly, it just changes the oder of your songs. Unless they changed it in version 4, it will play the same order every time. To solve, start it on a track that it never plays. It should follow to another track never played, and so on.
It has to deal with the math used to come up with the random numbers. If you turn off the repeat feature, then the random number generator is forced to use all possible songs.