Missing songs and Playlists: how to restore from Time Machine

in macOS edited January 2014
Here's my story. I Synced my iPod a week ago before vacation (and this was backed up with Time Machine). When I returned I launched iTunes to find all my playlists and podcasts had disappeared. I also noticed that on my iPod I had ~4500 songs; iTunes has only 4100, so I'm missing about 400 songs.

If I open up Time Machine and restore my my whole iTunes folder (in User>Music) will that, theoretically, restore all my songs?

If I've added new Music to iTunes (that wasn't in the TM backup), will those songs be over-written by the week-old backup?

It's too tedious (and not at all obvious) which songs are missing, so hoping Time Machine can come to my rescue.

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