I dunno. Reading this I can't help but feel like maybe the author is doing it wrong? I'm going to be charitable and admit that Apple has made iTunes incredibly difficult to use effectively, especially since the store is awful and they really, really push the iTunes store on you. That the interface is so slow and inconsistent doesn't help either.

My advice to anyone who has any desire to use iTunes is: acquire your music from elsewhere as actual mp3 files, tag them using something like Mp3tag[0] and then drag and drop them into iTunes. Make sure you check the "Keep iTunes Media folder organized" and "Copy files to iTunes Media folder when adding to library" options in the advanced settings. The only control you're really giving up then is the exact naming scheme of the files in the folder. But "<library directory>/Artist Name/Album Name/01 Song Title.mp3" is a pretty sane convention in my opinion. I have close to 18,000 albums in my iTunes library that I've added this way over the last decade and a half. It works pretty well and I have no problem reasoning about what music I have.

I totally agree with his complaints about Apple Music though, it's pretty inscrutable. But I wrote my own music streaming server with Sinatra and iOS app to go with it so I always have access to whatever is stored on my hard drive at home in a way that makes sense to me. If I'm not at home that's what I'd rather do, no syncing or anything weird.

0: http://www.mp3tag.de/en/