Question about iTunes

[CloudWatcher]

6. Depending on the iPod history ....

iTunes might not want to do this..... there were a lot of copy-protection issues early on. I'm not sure what the current state of the world is these days (and Apple's store downloaded music is no longer copy-protected).

But for a while you needed to either already be syncing the iPod with your computer (and/or iCloud) before it would consider your computer and the iPod to be part of the same pool.

E.g. a quick google turned up a couple of articles on this:

https://www.cnet.com/tech/computing/how-to-transfer-music-from-an-ipod-to-your-computer/
https://www.mobikin.com/idevice/transfer-music-from-ipod-to-computer-without-itunes.html