I have ripped most of my CDs, and digitized several of my vinyl albums (I have a couple hundred), and keep a couple of backups.
About 7,500 songs so far.
I then put everything in iTunes on one of my laptops, then mirrored on (first, many years ago) an iPod 80 gig classic. Later I picked up an iPod 6, and copied everything to it.
When I finally broke down and gave up my flip phone, it was an iPhone 6 (a little over two years ago, the last iPhone to have an earphone jack). Again, another copy of my iTunes library.
I got an iPad last August for my birthday, so yet another duplicate of my music.
The 80 gig iPod classic is docked in a 24 bit converter that is connected to my stereo system.
The iPod 6 is currently in Eddie, connected via USB to the Alpine stereo. I sometimes take it out to the shop and connect it via USB to the Harman Kardon stereo I have out there.
The iPhone 6 gets connected via USB to the stereo in Mrs. Racer’s Toyota Corolla, and the Alpine (also USB) in my Subaru Legacy goon.
If I want to use it in the Ram I need to use the headphone jack and use a cassette adapter (poor option). The Ram stereo is an odd size, with few options for aftermarket upgrades, and in 2001 when it was new OEM stereo didn’t support addons.
I also have an XM radio, with a lifetime subscription. I have a cradle in the Ram, the Legacy, Eddie, in the house on my stereo system, and in the shop connected to the Harman Kardon.
So, when I’m not tuned in to racing (four TVs in the house, two in the shop), that os what I have going.