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Is there a setting or some kind of user-script I can use to view all songs that aren't already on my iPod (from within iTunes, I'm sure there'a a command line way to just compare the files). I often add new music to iTunes but don't necessarily want it all on my iPod, so I need some way to browse new music.

FWIW the Date Added field doesn't help to identify new music, because I recently changed laptop so all the music is the same date. Besides, tastes change and I may want to add something to my iPod now which I didn't when it was first added to iTunes.

I imagine some script to add all non-iPod songs to a playlist, or perhaps just add some attribute to songs for filtering into a smart playlist would work, but I don't know how to do that yet, and I was also wondering if there's something native?

Using 12.9.6.3 iTunes app on Windows 10

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I won’t comment on command line file comparisons as it’s a can of worms of its own.

How do you add the music to the iPod?

If you use playlists: You can create a smart playlist that selects tracks not in your syncing playlist. Even if you don’t use playlists yet, I’d recommend you start.

Smart playlist sheet showing two playlists set to “Playlist is not”

In the photo example, you can imagine the playlists Best Playlist Ever! and Hot Stuff are syncing to the iPod. By setting these to Playlist is not, we’re excluding just those tracks but showing everything else in your library.

If you use Manually Manage Music: I got nothin’ for you. While you can see information on what’s on the iPod in iTunes, there’s no way I know of to compare it to the rest of the library.

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  • I have been manually managing music because I've used multiple computers to add songs over the years. I suppose I could click and drag all the music from my iPod into a pretend "best playlist ever!!" and proceed as you have done, but that sounds like it may create duplicates. Perhaps there's a way of exporting the contents of my iPod in XML format and importing that to iTunes as a playlist? Then using the "not" filter. Although I'm not sure if there would be a way to do that which automatically updated as I add more music
    – Greedo
    Commented Aug 25, 2019 at 11:38
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    Ah, as multiple computers are involved, it becomes more complicated. If you decide to sync playlists rather than manually manage, it will remove all the music currently on the iPod. While this will remove the possibility of adding duplicates, it, well, removes all the content. In a way, you can still manually manage your iPod, but you manage it through the playlist(s), which then syncs to iPod. I’ll link another cool tip on smart playlists shortly. Check my answer when I do.
    – The_Stewart
    Commented Aug 26, 2019 at 19:25
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Inspired by @The_Stewart's answer:

  1. Open the iPod in iTunes and make a new smart playlist (right click just below the last playlist on the iPod, or ctrl+alt+n on Windows)

iPod playlist

I chose to match all media with time > 0 seconds, i.e. everything. Name it whatever you want, I called it iTunes Export, and save it anywhere, you can delete it soon.

  1. Export the playlist as a text file (if you export as XML then you'll export the rules too, and upon importing to your library iTunes will just list all the music there instead)

Click File > Library > Export playlist

  1. Import that playlist into iTunes (same menu as Export, just one above), you may get a Some of the songs [...] were not imported as they could not be found message - click OK; it just means there are songs on your iPod which are not in iTunes, but that's not what we're worried about.

  2. Finally, create a smart playlist in iTunes as per The_Stewart's answer; make it so it excludes any of the songs in your exported & re-imported playlist. Here I filter for only music, but by exporting all media from the iPod you can make multiple smart playlists to filter my different media kinds

enter image description here

Optional 5th step: you don't need the playlist on your iPod any-more but it may be useful if you want to do this again in the future.

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