So, this question is not about iTunes Match or Apple Music. What I'm curious about is the Dropbox-like functionality of iCloud Drive. Basically, I'm tired of syncing my iTunes libraries on two different computers (I use an app called SuperSync currently). What I'd like to do is to store my entire music library on iCloud Drive. In theory, if I directed both iTunes apps on each Mac to the library on iCloud Drive (option-click the dock icon), I would essentially be sharing the same library between two Macs (or more) without having to pay for iTunes Match in addition to my iCloud Drive allowance. I could then use CarbonCopyCloner to make regular backups of that single library to an external drive. First question: Is this possible (i.e. can you foresee any issues with this setup)? Second question: I don't often use the two Macs in tandem, but one iTunes library remains permanently on. If I were to add music to my MacBook library, would that cause a problem for the Mac Mini's library, or would it simply be a matter of re-syncing the library by restarting the iTunes application?