In addition to Garthhh's comments, you could also add in the column
that tells you how many times a track has been played and when the last
play was - should give you more idea if it is repeating but my first
guess would be a corrupted file that sticks for a long time during the
track.
(right
Are you playing from a dynamic or a static playlist?
Take any playlist & shuffle playlist
Shuffle the playlist several times & scan the list to see...
set to don't shuffle
Play
you will have a much better idea of how many files have been played, there
won't be any repeats or skips unless they are