iTunes/Music success!
It took weeks of research, more than one try (each taking hours), a bunch of troubleshooting, and there are still a small number of errors and duplicates to clean up, but I have successfully transferred my 10,000 song | 100GB | 16-year-old iTunes/Music library to my new laptop.
Now I can start targeting my new laptop for Time Machine backups instead of my old laptop, so I've ordered a new 4TB external hard drive for backups. And I can start syncing my iPhone to my new laptop instead of my old laptop.
Eventually, when I'm certain I've really moved everything over and backed everything up safely, I'll wipe the old laptop and reinstall its OS from scratch.
Now, with everything transferred and loaded and reinstalled, the new laptop's hard drive has 1.46TB of 2TB available. This should be enough additional storage for several years :-)
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Over these 16 years, my most-played artists are: Moderat, Home Video, Oliver Tank, Heather Small, Grimes, Erasure, Mister Lies, Autre Ne Veut, Small Black, Sky Ferreira, Mano Le Tough, Elite Gymnastics, Genki Rockets, and Bvdub (bands I've seen live are in italics).
But of these 10,000 songs I've never played 4,513 of them. At least not in a way that my electronic devices have recorded. Some of these I played frequently from CD or my Windows desktop computer before I transferred them into my iTunes/Music library. I could spend 16 days, 24 hours per day, listening to these "unplayed" songs. I should spend some time doing that.
Now I can start targeting my new laptop for Time Machine backups instead of my old laptop, so I've ordered a new 4TB external hard drive for backups. And I can start syncing my iPhone to my new laptop instead of my old laptop.
Eventually, when I'm certain I've really moved everything over and backed everything up safely, I'll wipe the old laptop and reinstall its OS from scratch.
Now, with everything transferred and loaded and reinstalled, the new laptop's hard drive has 1.46TB of 2TB available. This should be enough additional storage for several years :-)
-----
Over these 16 years, my most-played artists are: Moderat, Home Video, Oliver Tank, Heather Small, Grimes, Erasure, Mister Lies, Autre Ne Veut, Small Black, Sky Ferreira, Mano Le Tough, Elite Gymnastics, Genki Rockets, and Bvdub (bands I've seen live are in italics).
But of these 10,000 songs I've never played 4,513 of them. At least not in a way that my electronic devices have recorded. Some of these I played frequently from CD or my Windows desktop computer before I transferred them into my iTunes/Music library. I could spend 16 days, 24 hours per day, listening to these "unplayed" songs. I should spend some time doing that.