As background, I bought my first Mac in 1985 and have used iTunes from its inception to manage a fairly large music collection.
That collection includes music purchased from Apple (very little), music downloaded from Napster and Limewire, albums ripped from my own CD collection (since sold) and music ripped from CD’s borrowed from others and the library.
iTunes got the job done fairly elegantly early on, when it just had to move music to an iPod, but its grown into the monstrosity it is today, asked to do way too many things in ways that ca n be very far from Steve Jobs’ mantra, “It should just work”.
Honestly, I haven’t visited iTunes in at least a month. And that’s usually just to synch photos to my iPhone and iPad. The less I have to open it, the better.
What’s working for us right now is to simply forget the concept of “owned” music and music libraries and get our music streaming from the cloud. Being Apple people we pay $14.99/mo for a family subscription to Apple Music, which seems cheap compared to what we used to spend buying CD’s, let’s say. Google, Amazon, Pandora and others also offer music services that may be as good or better than Apple’s offering.
In practice, this means not being concerned with the music that’s physically on our devices. Yes, Apple Music lets us download music to our devices, but unless we know we’re going to be out of cellular range, we rarely do.
To see how it works, we recently did a 3 week road trip to Florida. Once tired of the news and podcasts, we on a whim listened to albums by Don Henley, Pink Floyd, Ry Cooder, Ricky Nelson and a few others that escape me now. All available streaming via Apple Music. Back home, someone recommended the latest Drive By Truckers album and another friend recommended Jason Isbell and I’ve enjoyed both via Apple Music.
Anyway, just wanted to point out that abandoning the whole concept of owning and loading music onto a device from a music library can be readily abandoned with very little downside. It might be worth a try.