iTunes is obsolescent. But you knew that. Still it's worth reviewing the milestones along the way to its decline and fall. Let me describe my own experiences with iTunes and what cultural, financial and musical factors influenced me in my decision to take more direct control of my musical library.
When I first got an iPod in maybe 2003, it was a revelation. I had a portable mp3 player prior to the iPod, but the download interface was cumbersome, it didn't hold much music (even in mp3), and it was obvious that the compressed mp3 format was nowhere near the sound quality of a Redbook CD. The iPod solved two of those issues, with a larger storage capacity and a pretty darn good user interface with iTunes. I began taking all the CDs I had and loaded them onto my hard drive and began my sometimes-rocky relationship with iTunes.
Hard drives on iPods kept getting bigger, to the point where I could almost store all my music in compressed proprietary Apple Audio Coding (AAC) format. For the time being I was happy. I was even relatively happy when Apple started offering iCloud storage, primarily because when loading 1400 CDs onto a hard drive, two copies is one and one is none.
So far, so good, right? I stopped buying CDs and almost exclusively downloaded albums from iTunes, kept on a Mac, transferred to an iPod (or by this time iPhone) and was using iCloud storage, the perfect little Apple customer.
Around 2013, I began to have issues with Apple and iTunes for two reasons. First, they began to charge higher rates for iCloud storage. Second, I found out something that their more tech-savvy customers probably had already known. If I uploaded a file that was larger than a certain resolution, they would compress it. So, if I ever lost my data and used iCloud to re-download all my songs, they would have been compressed copies!
About this same time, disk storage began to become even less expensive for more gigabytes. In the spring of 2014, I got the Apple TimeCapsule network attached storage and began to re-burn all my CDs into FLAC and was pleased to find it fit all my music with room to spare. Also, around this time I began to care more about sound quality and upgraded my stereo. And I realized that streaming iTunes through an Airport Express was lossy streaming and I could tell.
So, what to do? I had already mentally committed to cancelling my iCloud account and created two hard drive backup copies. I wanted a program for my Mac that managed music like iTunes did, but with audiophile sensibilities in mind. I tried Audirvana for a while and liked it a fair bit, but once Roon was released I hooked, primarily due to the lossless streaming capability to any Roon-enabled device.
Roon did many things for me that iTunes could not accomplish. I could stream to any Roon enabled endpoint on my local network. Equally important, integration with Tidal changed the way I purchase music. When I hear or see about new music that might interest me, I'll try it out on Tidal and if I like it I'll buy the full album either as a digital download from HDTracks.com or if I -really- like it I'll get the LP. The point is that I can preview and sample with a streaming service, then prioritize which music I'm likely to want to keep in the long term with either a hi-res digital copy or vinyl.
The consequence of this is that I haven't bought an album off iTunes in four years. For my dollars Apple missed the window of opportunity by not releasing their own streaming service ahead of Spotify, Tidal and other streaming services. Once Apple combined iTunes and iCloud and started streaming with Apple Music, the death of downloads was obvious, and Apple was already behind the 8 ball. I'm gone from the Apple music eco-system, never to return. But Despite this complete divorce, I'm not planning on abandoning my iMac or iPhone any time soon, but I am hoping they will support MQA at some point in the future...