IPod Classic Contacts sync issue...

I've restored and re-booted my iPod Classic from the ground up - including re-syncing my 7 and a half thousand tunes - in an effort to see if I could kick-start the sync-ing of all the Contacts in my iMAC - but to no avail. I followed up by selecting "Manual Sync" as suggested on the Help menu and only chose to sync "Info". That didn't work either. However, the Calendar is now showing up on the Classic, but no matter what I do, it still shows "No Contacts"...

I almost shouted from the rooftops when I read your reply planb77 of Easter Island because it sounded like the perfect fix!
Sadly, I switched the System Prefs in Contacts back to On My Mac as you suggested and still no joy.
I also went into the "Accounts" tab to the right of the "General" tab and switched that to "On My Mac - Local" to see if that would make any difference and again, nix.
Unless of course I have to re-boot after the switching...
Sincerely, thanks for the assist - back to the drawing board : (

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    Once iTunes went to version 11 my iPod Classic stopped syncing.  My iPod Touch will sync.  I prefer my Classic though.  It is recognized by iTunes, starts the first step of the sync process but that shuts down and doesn't sync.  It doesn't freeze my machine just won't launch the sync process.  My library is on my iPod from the last time it would sync, but anything I've bought since won't load to the device.  I ran the diagnostic and it fails at the end saying no device found, which is weird since it appears in my iTunes, tells me how much audio and files I have and reflects that I have 16GB available.  I've tried tons of the tips on here, changed settings, checked and unchecked all kinds of boxes, changed USB ports, etc., and nothing has worked.  Has anyone else had this issue since the v.11 series of iTunes came out?
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    ASUSTeK Computer Inc. K54C
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    QuickTime 7.7.3
    FairPlay 2.3.31
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    CD Driver 2.2.3.0
    CD Driver DLL 2.1.3.1
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    Apple Mobile Device Driver 1.64.0.0
    Bonjour 3.0.0.10 (333.10)
    Gracenote SDK 1.9.6.502
    Gracenote MusicID 1.9.6.115
    Gracenote Submit 1.9.6.143
    Gracenote DSP 1.9.6.45
    Current user is an administrator.
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    iTunes is not running in safe mode.
    WebKit accelerated compositing is enabled.
    HDCP is supported.
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    Intel Corporation, Intel(R) HD Graphics Family
    **** External Plug-ins Information ****
    No external plug-ins installed.
    iPodService 11.0.2.26 (x64) is currently running.
    iTunesHelper 11.0.2.26 is currently running.
    Apple Mobile Device service 3.3.0.0 is currently running.
    **** Device Sync Tests ****
    No iPod, iPhone, or iPad found.

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