Great article but I am glad to say I don’t have to feel the pain of using the worlds worst music program ever, iTunes. I am not much of an Apple fan, their products are too overpriced and there’s nothing I can’t do on an Apple device that I can’t do on a Windows PC (or Linux), and Android phone or tablet and a Roku, Chromecast or AndroindTV and I can probably do it better on all of those while avoiding the closed ecosystem of Apple.
I enjoy uploading music to my mobile devices through folders as opposed to a specific program, better control, I enjoy the freedom of customization and I also enjoy the multiple options I have for software and hardware.
I have a pretty big collection of music myself, all DRM free, but likely not as big as yours. I have total access to it from any mobile device, any PC and any media player in my network and even outside of it and I am not dependant on iTunes to use any of it. The only reason I have iTunes on my PC is because I have an old 1st Gen iPod Touch which I have as a backup to my music when my Android Tablet dies on me or my wife is using it. But if I could upload music another way like I could with the old iPod Shuffle (the long thumbdrive looking one) I had and some hacking tricks I found, I would remove iTunes all together. But, low and behold as long as the iPod lives so will iTunes on my PC, even if hardly touched.
To each his/her own. If Apple is you thing then more power to ya. Competition is always good and choices are even better. I simply choose to steer clear of Apple when ever possible.