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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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What an absolute game changer (the Music App was losing album from my collection constantly). I have followed the instructions and have gotten iTunes up and running on an M4 Mac Mini. I have one question / request for help - How do I not have the iTunes folders and files show up on my desktop on start up? How do I keep them in the iTunes Folder in the Music folder? (If i move the files from the desktop to the iTunes folder - iTunes will just make a new set on the desktop upon reopening the program.)
 
Question, with those of you that are still using iTunes (hi y'all! :D), does your iTunes show up in your native 'Now Playing' section in the top menu? Like the 'now playing' button on your Mac? Because my Mac (running Sequoia 15.6) doesn't seem to be recognizing iTunes as a media source for that area, it only shows something is playing as a notification in my notification drawer, and this is something I'd really like to fix if it's possible!

I'm using iTunes 12.8.3.1, installed via Bogdan's method (although previously it was through Retroactive).
 

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Question, with those of you that are still using iTunes (hi y'all! :D), does your iTunes show up in your native 'Now Playing' section in the top menu? Like the 'now playing' button on your Mac? Because my Mac (running Sequoia 15.6) doesn't seem to be recognizing iTunes as a media source for that area, it only shows something is playing as a notification in my notification drawer, and this is something I'd really like to fix if it's possible!

I'm using iTunes 12.8.3.1, installed via Bogdan's method (although previously it was through Retroactive).
When using iTunes 10.7 on Sonoma and Sequoia, I don't recall ever seeing iTunes in the notification section on the menu bar since it is not recognized as an "approved" app. Are you looking for an app that will display the current song and artist being played in the menubar? If so, there are some older utillities that can do that such as iTunesPlay or Simple iTunes. Both of these still work with Sequoia (and Sonoma as I recall) but I haven't updated to Tahoe yet so can't say about that yet. For really long song titles that cannot fit in the menubar, it just shows nothing instead of cutting off the end of the title.

Since these are older apps, you would probably have to use the Internet Archive to download them. Here is an old Apple Discussion thread that describes one or two:

 
One other thing I forget to mention about the two apps I referenced earlier is that they also work on PowerPC Mac's as I use them on those as well as other newer computers like the M1 under Sequoia. Whether they will still work under Tahoe remains to be seen as I still need to upgrade and will report back.

EDIT: After checking my PowerPC G4, I realized that iTunesPlay is the one that works on that platform. Simple iTunes works on Intel. However, both do work with iTunes 10.7 under Sequoia.
 
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I updated the M1 Air today to Tahoe and while iTunes 10.7 still works, the CoverFlow format is not displaying properly as the album art ends up on the bottom of the screen covering the song information with only a part showing on the right side. The other three modes display properly: List, Album List, and Grid. Also, my favorite screen saver Cover Version still works and clicking on the right spot to enable full screen CoverFlow still displays properly so overall, it's still fine for playback of music which is my main use. I also have a Sequoia volume to boot from as there are no issues with iTunes 10.7 there.

I use Simple iTunes to display song title and artist in the menu bar and that still works in Tahoe.
 
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