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The reason why it seems convoluted is because there was an original account that was used to purchase the music currently on the iPod. Any new music would need to be purchased with that same account in order to "add" it to what's there. A newly created account is just that: new. So, you can't have two accounts active on the iPod -- which means you need to either:

Stick with the original account, or:

Stick with the new account.

Hope this helps!

Or contact tech support. Maybe they can help.

Your standard MP3 player will allow you to copy and move files from one player to the next all day long. Not so with the Ipod.

This might be due to the licensing agreement between RIAA and Apple since it would make easy to clone the music.

It is a bit of a pain in the rear and it would be really nice to be able to “transfer” the songs on an old device to a new device without involving Itunes. Especially third party MP3 songs that were converted from a CD, etc. which are also on the older Ipod.

Also, important to note: Apple may not have a complete list of previously purchased songs even if the user was able to find the original email/account name.

And early on, Apple used account names versus emails as the customer id. A few years ago, Apple required everyone to change their user id to an email. So the original id may be a name or it could be an email.

I have personally experienced all of the above and it can be a bit frustrating.

“The reason why it seems convoluted is because there was an original account that was used to purchase the music currently on the iPod. Any new music would need to be purchased with that same account in order to “add” it to what's there. A newly created account is just that: new. So, you can't have two accounts active on the iPod — which means you need to either:
Stick with the original account, or:

Stick with the new account.

Hope this helps!”

All true. We have had 5 or 6 different computers with our iPod/iTunes account.

You can preserve both libraries, if you have two accounts.

Steps:

1) Log into the original iTunes account
2) Authorize your computer as an additional authorized computer. You can have up to 5.
3) Restore your library from the iCloud. If you can't you may have to call Apple support to get it done.
4) Sync with your iPod.
5) Share with another account, your other iTunes account. If you can't do this on your same computer (I've never tried that) get another computer on your network with that account and share the tunes.

This is all described somewhere in iTunes, but this is my distilled experience of 10+ years with an iPod.