[Please skip to Post #3 for the latest update!] Hello everyone, I've spent the entire weekend so far trying to get this resolved. I hope the experts here will be able to help me out. I took the plunge last night with Apple Music. I already have local music files stored on my iMac that I have obtained from various sources over the years. What I want is for me to 1) listen to the entire library on my iMac at home 2) listen to the entire library on my iPhone and 3) listen to the entire library on my iMac at work. Three devices. All the music that I own. Apple Music promised this to be a seamless transition, just as long as I turned on iCloud Music Library. I did that on my iMac at home and iPhone and... something weird happened. Songs either disappeared or they were duplicated on my iMac at home. I've tried every which method to have this resolved but to no avail, so I have turned to alternative streaming sources instead. Spotify seems like a good choice, and what I want to do is to transfer all my songs on my iMac at home (local files) onto Spotify, so that I can stream everything, everywhere. So far, however, I haven't been able to do so. I do not consider myself an IT luddite at any rate. I am fairly well versed with other areas of my Apple universe. iTunes, Apple Music and music streaming in general, however, seem to confound me to no end. Even after trying Apple Music out last year, the service is still a tangle of complexity for me. Please help! I appreciate it, guys.