My data may be potentially overflowing

I have (at the time of writing this) 1,113 songs on my iPod, and I've noticed that occasionally a song will repeat itself. On top of that turn the device off(not sleeep mode) will wipe the cue if it's in the main song list, restarting from no.1 (what ever song it left off on will be the new first and the list is shuffled) but can still remember the time in the song which it left off on. This happens in most long playlists as well, i.e. About over 600(could be less, could be more, I noticed it after I added a very large batch of music) but the second it's playing a playlist that's shorter, it will function as normal. (Like I said, I noticed it after I added a very large batch of music, back then I was around 300-ish songs with 190 pictures and 2 extremely short videos before the large batch addition which brought it up too about 836 songs, 227 pictures, and 1 video) There is currently 5.7 GB out of the available 14.7 GB

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