iTunes as an application is by far the worst UX present on a Mac or a PC, which is especially surprising considering how nice the vast majority of OS X apps are to use. You can go down the list of the recommendations Apple gives out to developers on how make what they consider great apps for OS X and iTunes breaks every single one almost as if it were intended as a use case for terrible UX.<p>The navigation and structure changes with every movement, there are occasionally two seperate back buttons present that can either do the same thing or completely different things, the &quot;background activity&quot; or as I like to call it, &quot;What you need to know is happening to your iPhone&quot; is constantly buried beneath the currently playing track, and is not readily accessible unless you click a 8pt square down arrow, on and on...<p>Not to mention, as an owner of multiple machines I prefer to use ownCloud to sync my various libraries. Windows and Linux this is absolutely not an issue. Because iTunes insists on owning the directory and file structure though, I can&#x27;t just point it at the folder or it will literally ruin it, I have to instead keep two copies of my library on my Macbook, and occasionally use an rsync alias to move over new stuff. Thankfully I usually do all my purchasing (on Amazon MP3) on the Macbook anyway so it&#x27;s of little consequence, but it&#x27;s just one more irritating thing to add to the list.<p>I&#x27;m an Apple fan, I admit, but iTunes is a fucking train wreck.