Autofill not working after Restoring Shuffle

I have an old shuffle (bought in 2006). I was forced to restore it in order to put new music on it.  After restoring, I clicked "autofill" and it won't work - it says all the songs in my library are already on my ipod, but they aren't, it was wiped clean after restoring.  I tried to click and drag one song and got an error msg "must download from icoud first".  Went to Apple store for help and they are closed for renovations, an employee outside the store told me to call apple care and of course they wanted to charge me for help on this matter.  What do I need to do to put my library songs on my ipod....I restored it twice just to make sure the songs weren't somehow still on there.............

Actually?
THIS ***** SO INCREDIBLY!
At least before following this well-intentioned but misguided advice I still could track down all the old, CRUCIAL banking info, addresses, insurance and utility info (by looking into the keychain access) .... but now I've lost completely crucial passwords and usernames FOREVER.
(And I'm out of the country for a few weeks. And has anyone actually TRIED to phone Apple support in Canada???????? I DARE you. You cannot get thru. It's impossible. This update has totally screwed up my computer.... And being unable to get support either thru Apple or thru discussions is like Chinese water torture combined with someone slowly pulling out your fingernails one by one.)

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