I thought I’d put in my two-cents about the confusing way Apple Music, iCloud Music Library, and Apple Music work together. TLDR: Despite doing the "wrong thing," users are not at fault. Apple simply fucked up.
They don’t mean to rub me the wrong way, and are upstanding people I’d be truly honored to meet, but many Apple journalists are being Cupertino apologists. Update: Serenity wrote a great article. Regrettably, I misdirected my frustration. As a semi professional musician I got caught up thinking of losing a valuable collection. I'd be quite upset to lose it. I'm sorry. I am not going to explain how this hodgepodge of services interact with each other and how Apple’s apparatus works here, there are plenty of places that deconstruct this maze. I’m an Apple nerd and understand the system, but so many intelligent, savvy people have had trouble with this ridiculous behavior.
Clicking OK on a confusing dialog box that requires awareness of arcane behavior should not delete a massive local library that someone spent years curating. This is a fundamental UX design blunder that reminds me of some of the bureaucratic bullshit and terrible design that occurs at old-hat institutions with severe lack of software development resources. At these places, an unwillingness and inability to rethink the legacy red tape perpetually harms user experience. Apple is not that type of company. They have no excuse.
With my maxed-out Macbook from late 2012 with a recently installed 1TB SSD I’m lucky enough to have crazy redundancy even on my local Mac. I keep a "Music.bak" folder in addition to the default iTunes Media folder. Time Machine and Carbon Copy Cloner backups occur on two external 2TB hard drives. Uploading my entire home folder with Arq to a Dropbox Pro account rounds out my paranoid defense against Apple’s services.
Unfortunately, normal folks don’t know better and don’t have these backups. They shouldn’t be humiliated and scolded in forum threads because they don’t know computer hygiene. There should be some way to spread awareness, but without someone like me or a David Sparks at family holidays, these people are too busy with their lives to have this knowledge. All they know is Apple stole the music they ripped from hundreds of CDs that are now in the landfill or the attic.
I’ve found that iTunes database is the most convenient place to put music on the Mac, and after using all of the streaming services available I’ve concluded Apple Music is the most pleasant and seamless service. Apple has gotten a lot of things right with music, and the Beats acquisition was genius. It’s amazing that iTunes works so well, considering that it’s codebase is composed of layer upon layer of old and new "features." It is a great feat of engineering. One of my old bosses told me that software like iTunes is like the old NASA space shuttle. It is impressive, built for reuse and has the ability to have infinite features tacked on to its frame. In the case of music, it’s a better idea to build a well thought out space capsule that only addresses a few problems.
Due to the need for cross-platform support, Apple does not have the luxury to completely scrap iTunes and start over from scratch. But maybe putting a bit more resources on the project could yield iterative improvement.