3rd gen iPod Nano will not sync with latest version of iTunes. It passes the connectivity test but not the sync test under diagnostics.  Worked fine on old Windows 7 laptop but not new one.  From Control Panel it shows up as an Apple iPod USB Device...

3rd gen iPod Nano will not sync with latest version of iTunes on new laptop. It passes the connectivity test but not the sync test under diagnostics.  Worked fine on old Windows 7 laptop but not new one.  From Control Panel it shows up as an Apple iPod USB Device...

Never mind, I think. I think I figured it out. There was 1 song (out of > 900!) that somehow had been purchased with the other ID - I have no idea how. Once I deleted that song, it stopped asking.
There may be something with the newest iTunes version too. I didn't think in older versions that the "On this iPod" list of songs was greyed out. But at least it syncs ok.

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