Not had time to pull that old laptop out, but have a look at this thread: "Syncing" iTunes Cover Art with Picard
And especially @st3v3p as he actually uses Apple iTunes. So does playing the tracks not fix this like he suggest?
I am kinda disappointed at the lack of Apple users in the forum 
Was hoping someone who actually uses iTunes may know how they solve this. I just ain’t had the time to pull that old laptop out and setup a test.