IPod touch randomly skipping songs

I have recently overhauled my entire iTunes music library and sorted out all of my albums, album artwork and artist names etc in preparation for syncing all these songs onto my iPod (well over 240 albums, 3,500 songs and roughly 30 gig of music data)
I selected "Songs" and have shuffled the entire library so I get a mixture of tunes while walking my dog. I have noticed that the iPod will randomly start and stop songs, this mainly happens near the end of a song - the track length is 4:18 and it will stop at 4:15 and go to the next song. I have checked my settings and the option to shuffle tracks when the iPod is shaken is turned off.
I have also experienced that there has been approximately 30 seconds left of a track and then it will go into an entirely different song from another artist. When I click the arrow to go to the next track it will pick this exact song and the time or section of the song it's up to (for example 2:04 into the next song).
When I say that I've overhauled my music library, I converted songs in iTunes to AAC 256kbps format (iTunes plus), I noticed some longer songs defaulted to a time of 4:58 (usually these were 6 minute + songs) so I converted these to AAC 256kbps using a third party program (MediaHuman Audio Converter).
I currently have all of my music residing on another hard drive separate to my Windows 7 OS. I'm at a loss as to what to do as I've restored my iPod several times, manually deleted music and re-added it all with the same errors. They do not seem to happen on particular music tracks as I place the iPod on shuffle often so it will be random what I hear during a walk.
Any advice or replies are appreciated - it really has me stumped as to what is going on.

Close the music app in the multitasking bar. Then try again.
Restart/Reset/Restore your iPod. (in that order).

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