HT2729 Help pls! About to toss my ipod out the window!

i recently downloaded a free video, kip moore's there's something about a truck to my itunes, yet no matter how many times I sync my ipod it won't transfer. What am I doing wrong? It's been years since I've put anything on here due to pc issues and I don't remember it being this hard....
Also, about a year ago it just stopped playing on any docking stations, will only play thru headphones and some cheap thing that i got that plugs into the headphone jack.  Any idea why this happened? It charges on all docking stations, just doesn't play.
Any help would be soooooooooooooooooooooooooooooooooo appreciated!
Thanks in advance!

You are probably experiencing a bug known to this community but unacknowledged by Apple. There is a flaw in the way iOS manages the music library, a flaw easily triggered by the syncing process with iTunes.
Let me commiserate. I have an iPod touch iOS 6.0.1 set to manually manage music, and it gets automatically mangled with this data deletion bug multiple times each week. Each time, I have to start all over again trying to find all the music tracks that belong on it from my archives, re-organizing the playlists in some former semblance.
This bug seems to affect iOS 6.x devices set to manually manage music the most, but other versions of iOS and device setups are affected. From what I've frequently experienced, and read from the accounts of others, is that suddenly you will find in iTunes that every track on the device is gone but there is still a record of it existing along with associated metadata (such as playcount). Each track will have an exclamation point picon next to it, indicating that there is a record of the track existing but that iTunes/iOS deleted the reference to it. When disconnected, the Music app on iOS will show no songs and provide an ad link to go to iTunes Music Store.
If you are fortunate after this point, additional sync sessions with iTunes may begin to restore the music again. This can be a very long experience as each track has to be transferred anew. Hope for this occurance decreases if you have your device set to manually manage music. Hope decreases further if the collection of music tracks is a variety of files from different sources not included in your computer iTunes library.
I have been carefully following this bug and no one has a viable workaround. We are patiently awaiting an update from Apple. I suggest sending feedback to Apple each and every time this bug affects you:
http://www.apple.com/feedback/ipodtouch.html

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    Message was edited by: xxjudgmentxx

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