New Windows 8 computer not syncing most songs on older iPod.

I have a new Windows 8 computer and an older iPod.  I can now only sync songs that were NOT already on iCloud, even though all my 8000  songs are in files on my C drive and backed-up on an external drive.  The weird thing is that few files that do sync are the only ones that are also visible on Home Sharing. 

Hello Terrymcadam,
It sounds like you can press the sync button in iTunes but no music transfers over to your iPod classic.  I found an article that should help with transferring music to your iPod classic.
iTunes: Syncing media content to iPod
http://support.apple.com/kb/ht1351
You might need to go to the Music tab seen here and check the "Sync Music" box and then select the data that you would like to sync.
I hope this helps get you back on track!
Best,
Sheila M.

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