Problems Syncing New iPod to iTunes

The “Windows device” would be the device running Windows.

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I wish I could be more specific, but I've never done what you're trying to do myself. Why not just surrender to streaming? Why stick with an old technology that will be less and less supported over time? Are you going places where there's no connectivity? Is pricing an issue? I keep adding to my music library from the Apple Music library, and download is an option. Yesterday I added about 10 hours of music. We pay a flat fee for an Apple One Premiere subscription bundle which includes AppleTV+, Apple Music, Apple News+ and Apple Arcade, but you can get just Apple Music by itself for $11/month and have access to a huge library, or use Spotify, Amazon or Google and do the same.

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I stick with it because I have the CDs, I don’t have to pay a subscription and I don’t have to worry about bandwidth or data usage. But then it’s working fine for me.

How do you add to your collection?--Percy

Generally by buying CDs - often cheapish ones.

I already tried running it. THERE IS NO MENU! How do you get a menu to display?Apple has always boasted about how "easy" and "intuitive" it is to use. Instead, it is impossible to use! What is wrong with them? In part because it does not offer the music that I have ripped from CDs. I have absolutely no doubt that streaming would only provide me with 10% of the music on my iPod, if even that much! Why opt for something that is so vastly inferior?Also, there's the problem of losing content. I've used TV streaming a lot, originally with Netflix. Great shows and movies that are no longer there. Music streaming would carry the same hazard. That's why I keep the movies I want to keep on my DVR; even though there's the danger of losing them when the DVR breaks down, it's still less danger than with streaming.  Because it works! And the new stuff doesn't!At work we loved our iPods. Just carry it in your shirt pocket and reach into the pocket to control it by touch. A co-worker would play his while riding on his motorcycle using the same control-by-touch method. When they dumped the iPod and "replaced" it with the iTouch, we both just shook our heads in dismay. Try to imagine him riding his motorcycle and having to try to work his iTouch. No, I already told you what the issue is: LOSS OF CONTROL-BY-TOUCH CAPABILITY. Their "iPod replacement" suffers from a huge loss of functionality. And I'm sure that whatever has since "replaced" that is even worse. What the hell are you talking about? That has ABSOLUTELY NOTHING TO DO WITH WHAT I SAID! NOTHING! I never said any such thing!Rather, YET AGAIN, I was having to keep her phone awake WHILE WAITING TO START THE SONG, NOT DURING THE SONG. Finally she had to give me her password so that I could start it up again when it had shut down, but the music app would still go crazy at times through normal use.

Back in the days of CD's, after ripping it all to iTunes I probably had about 50 hours of classical music and maybe 40 hours of pop. Now, as long as I keep paying the monthly fee, I have 500 hours of classical and 120 hours of pop. I know it sounds like more than one could ever listen to, but it's not, not if you're just playing it in the background while you work. I go through my entire classical collection every month or so, which is why I keep adding to it. I don't add to the pop very often because I only add songs I like. I've already added all the older songs from the 30's through the 80's, and when there's a new song I like I add that.When I add a song I don't generally download it these days, but I could. It's protected so that you can't play it if your subscription runs out, though I hear there's pirate software that will remove the protection.--Percy

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Rather, YET AGAIN, I was having to keep her phone awake WHILE WAITING TO START THE SONG, NOT DURING THE SONG. Finally she had to give me her password so that I could start it up again when it had shut down, but the music app would still go crazy at times through normal use.

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I have never seen that and the basic controls of Apple Music can be operated from the Lock Screen (play, pause, fast-forward, rewind).

If I wanted a whole lot more music maybe I’d agree, but I don’t need it. I’m happy to add a little now and again and enjoy listening to what I have - although probably rather less often than you.