I have an old library with a mix of purchased and uploaded songs from CD. I also have a new Apple ID because my work phone forced me to create a separate one.
I have authorized my PC for the music, but it will not transfer to my phone. What is the solution other than paying apple like $500 for new versions of the songs I already purchased?
Windows, Windows 6
See Authorization vs. association - Apple Community. When syncing with iTunes you can include protected content from up to five different Apple IDs. If you have an Apple Music subscription that will only accept local media from the same Apple ID. You can either manually add tracks to the cloud library that you'd previously purchased with a different ID, or convert the tracks you have to new copies that can be matched or uploaded.
If you're simply having trouble syncing locally stored content from your computer over USB then it may help to delete and then reinstall the Music app on the iPhone. Presumably you are not actually running Windows 6 (Vista) but something sensible like 10 or 11 with the latest version of iTunes for Windows.
tt2
Items acquired with one Apple ID cannot be transferred or merged with another Apple ID unless you change it according to:
Change your Apple ID - Apple Support
Sorry, there are no other options.
Transferring iTunes music library
