Same songs repeat in shuffle mode

I have my playlist set to shuffle but I'm hearing the same songs over and over, while other songs never get played at all. There are about 250 songs on the list and I'm hearing the same 100 all the time (roughly). I am thinking there is some smart setting in iTunes that I need to untick or correct, but no idea where it could be. I know other people have had similar problems in the past and if anyone knows how to fix this problem with the current iTunes software and could tell me...thank you!

Make sure the Skip When Shuffling option is not enabled on these tracks in iTunes. To check, right->click on a track or tracks and choose Get Info. When the GI window appears, click the Options tab.  Here you will find the Skip When Shuffling option.
B-rock

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