I've been using iTunes for many, many years and have a few terabytes + of lossless music on an external drive, always keeping "copy music to itunes" and "let itunes organize" checked. I also keep a separate drive of the lossless music that is not tied to iTunes--just in case. I just switched from iTunes to Music and I'm rethinking the whole "let iTunes do everything". One of my major issues is backing up the iTunes library 2x and also backing up the Lossless HD 2x. This also means having files on the drives that aren't synched as far as tags. Out of curiosity, I just started a second iTunes library where I'm importing songs from my lossless drive and "copying to itunes" and "let iTunes organize" are unchecked to see how it goes. This allows me to change tags in itunes/music and it match the lossless drive. Only one drive to back up, which I will do twice. I like the idea of one, well-organized music drive, and my OCD is pulling me in 2 directions. Downside: This will take some serious time to change over and if something screws up in iTunes, it will also be on the original HD; I'll have the back-ups if I catch it before the next back-up. Sorry for the long post, but I would greatly appreciate any thoughts and opinions on how you store music when using iTunes/Music these days, especially the "copying to iTunes" and "let iTunes organize" boxes. I've looked elsewhere on the web, but this forum has always my best resource. Thanks!