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Did you have to reinstall iTunes after the OS update, or was the previous installation (and preferences) still functional after the update?
Previous install was good! It just turns the iTunes app icon I previously had in the dock into a question mark for some reason whenever I update. But as long as I get it back into the dock where the newly formed question mark is, it works like it did with zero issues. I have to open it from the Finder then have it stay in the dock and remove the question mark that was left behind after the update. No clue why it does this but it does work without re-install so that's good, and doing this is not that big of an inconvenience for being able to use iTunes!
 
I'm not sure what Music.app is not enough with modern iPhones. I sync my iPod Classic directly with Music.app on my Monterey M1 Mac Studio and it works great.

I have a single music library, not managed by any apps... just one named folder per artist, with one named subfolders per album. I do not stream music. I own all of my music outright. That way, my music isn't hostage to any streaming services whims. The music is also all DRM free (this took a little work to accomplish) and will play on any Mac.

I then just told Music.app on my Monterey M1 Mac Studio to import the top level folder and the rest happened pretty automatically. It absorbed the entire folder hierarchy and did the right things with it. I then did the same thing with my painstakingly developed playlists... I exported them from an older Mac and imported them in Music.app. Worked like a charm.

That said, while I can manage all of my music and playlists via Music.app, I cannot sync any of my older iPhones and iPods to it - just my iPod Classic. For my older devices, I sync them to the native iTunes on my Power Mac G5 Dual running Sorbet Leopard. That G5 had the same music folder set on it that I put on my Monterey Mac Studio and I imported it into iTunes the same way. From my G5 then, I manage my older iPods and iPhones.

By the way, I followed the same approach on my Sonoma M3 MBP and it worked well too.

So... I really think the simplest solution is Music.app for your current devices and a G4 or G5 running Leopard and iTunes for your older devices. A common music set is the key enabler.
 
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That said, while I can manage all of my music and playlists via Music.app, I cannot sync any of my older iPhones and iPods to it - just my iPod Classic.
What happens when you try to sync one of your older iPhones or iPods?

You could try updating the MobileDeviceOnDemand and CoreTypes packages. @bogdanw provided the terminal commands to get the current package download links in this post. After getting the links, you can run curl to download the .pkg files. Double-click each to install, then reboot and try syncing a device.
 
What happens when you try to sync one of your older iPhones or iPods?

What happens is just that the older device simply isn't detected at all, or at least it doesn't show up in Music.app or on the desktop. So, I sync them using my older G5.

Oddly however, I would rather go the other way. I would love to have my Sorbet Leopard G5 recognize and sync my iPod Classic. I *think* that it is the only music device I have that the G5 and iTunes can't deal with. Then it would all be together on one Mac. As a vintage Mac enthusiastic, I would prefer that "one Mac" to be my G5!
 
It just turns the iTunes app icon I previously had in the dock into a question mark for some reason whenever I update.
I don’t know why this happens, but after the update the Dock preference file has iTunes as located in /System/Applications ("file:///System/Applications/iTunes.app" in defaults read com.apple.dock)

As you said, the easiest fix is to open iTunes and choose again Keep in Dock.
 
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