TS1503 3010 songis on itunes and only 797 will sync

Hi All
I need your help.
my ipod touch 32gb (3rd gen) died so i bought a replacement, i got a 64 4th gen from ebay. the new one was reset to factory settings and the simple back up from library set up looked easy.
it was and i was happy, until that was i realised that only a 3rd of the songs synced, i have tried several things.
unchecking the Sync music box on itunes and removing all songs, syncing, rechecking the box then resyncing, no joy.
i tried reseting all warnings and clearing the cashe (prefrences- advanced ) no joy.
i tunes is upto date.
im getting desperate.
help

Bless you, dear Jimz!   It's great to reach out and find someone listening. Thank you!  Here's some background.
1) My ipad Air is brand new, and I'm trying to sync my iTunes library from an older Mac (10.6.8)
2) All of my PURCHASED music syncs successfully -- no problem there.  BUT ... none of my CD music from the 1990s, or my friends' music from their CDS, syncs with the new iPad. Only purchased music will sync.
3) I'm running iTunes 11.4 which is the latest update that my 2011 Mac seems to be capable of.
4) I had hoped to use Home Sharing, but it appears that my Mac's operating system is too far out of date for that, and can't be updated for free anymore. (?)
4) I did visit the iTunes Match page before posting my question but the info was vague about "music that lives on local devices." And before I pay the $35 for iTunes Match, I would like to know that all my weird old songs will sync to the iPad! It appears that iTunes Match will store ALL my music in the cloud, but I've also seen posts by people complaining that they couldn't access music that iTunes couldn't identify or find in the iTunes Store.  And my music is definitely not in the iTunes store or anywhere online.
So.... how can I get my full iTunes library, with oddball tracks -- to sync with my ipad air? Is iTunes Match the solution, or would I be better off waiting until I can get a new Mac, and use Home Sharing?  Or am I still asking the wrong questions?  THANKS.

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