Same here! 
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i have a playlist or 2 where i have it sorted by track # in the playlist. you would think each track would have its own track #, but i have large groups of track that are all the same track number. anyone know what's up with that?
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Same here! 
There is the Playlist "#" and "Track Number" They are two different columns. Is that what you mean?

Its the Playlist"#" that is mest up..it starts on 1 and goes to 99 after that its just 10-11-12-13 on the rest of the tracks..as shown on my pic. I just checked all of my playlists, and if there is more than 99 tracks this happens!
Ahh.. i found the solution... there was not enough space for the numbers :)

lol wow... that fixed it... #smh