Playback position on iPod not Syncing to iTunes. Nano 5, long mp3 files. I have remember playback position selected in Options, and that works fine. But position (45 minutes) on iPod and 2 minutes on iTunes do not get together

Long audio files (mp3 books) on ipod nano 5 play fine, Ipod remembers playback position (I set the flag in info-options) but after listeniong for a while on ipod, I expect that a sync to PC should update the playback position in iTunes. Thus I should be able to subsequently sync a second device to iTunes and have the position passed along to the second device. This is not working for me. I have the latest nano software, and iTunes 11.1.2.32. Have just re-installed iTunes per troubleshooting suggestioons on support web page.
Is this a format problem (mp3 issue) or something else?

Reply seems to be theway to elaborate on my origi;nal post.
I have now tried turning off Manually manage music and video on the iPod. One of the 3 long audio files (books as mp3) reloaded to the iPod when I made the chnge, but no loss in my case.. Playback position on iPod seemed to load into iTunes (looked good while iPod was connected in Playlists and Library/Music, but as soon as I disconnected the iPod the saved positions reverted to the old values. One more theory shot down. Since my goal is to keep several playback devices in step, I am back to jotting down the latest position and manually forward spacing the alternate device to pick up where I left off.
This seems so logical a use that I am baffled about why it is so hard (impossible?).
Jack

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