iTunes has been a mess for years, and Apple hasn’t fixed it, or even improved it. In fact, they keep adding more stuff in:
iTunes has an impossible combination of tasks on its plate that cannot be done well.
iTunes is designed by the Junk Drawer Method: when enough cruft has built up that somebody tells the team to redesign it, while also adding and heavily promoting these great new features in the UI that are really important to the company’s other interests and are absolutely non-negotiable, the only thing they can really do is hide all of the old complexity in new places.
So, how might we fix iTunes? I have a proposal, which consists of two parts: elimination and splitting iTunes into several apps.
First, elimination. iTunes should no longer let you sync an iDevice’s contacts, calendars, ringtones, books, photos, audiobooks, etc with your Mac. Those are best synced with the cloud.
iTunes should also do away with the ability to back up your iDevice to your Mac. Instead, your iDevice will back up to iCloud. Since people don’t plug in iDevices regularly (except to charge), and given small SSD storage on Macs, this should be straightforward.
That goes for iOS apps, too. It makes no sense for iTunes to download them on your Mac, where they can’t run, anyway. All they do is waste precious storage space on your SSD. Let your iDevice download them directly from the app store.
The iOS app store should also be removed from iTunes, and made into a separate web app. iTunes, when used to access the iOS app store, is a poor man’s browser. The navigation is awkward, with a lot of interface chrome that has nothing to do with the store. This is confusing, and disrupts your browsing if clicked. You don’t have basic functionality like reloading a page that’s stuck or didn’t render properly. You can’t Cmd-click a link to open in a new tab without interrupting what you’re doing. iTunes doesn’t honour your minimum font size in your browsers. There isn’t a URL you can copy paste to a friend or to email yourself to do later. It’s almost like Apple hasn’t discovered the web, and built its own one-off, half-assed, confusing version of it. And moreover stuffed it in an app with a lot of other functionality.
So, remove the iOS app store from iTunes, and make it a web app, similar to Google Play’s web app. Why a web app rather than a separate native app? I think it would be confusing to have a store app on one device (your Mac) that downloads apps on another device (your iDevice). I’ve never seen this kind of “remote app store” app before, on any platform. With a web app, this confusion doesn’t occur, since people understand that it’s not running on your computer and has little to do with it .
So, make an iOS app store at iosapps.apple.com, and remove it from iTunes.
Then, make a separate Music app. The app will show you all your music from all sources, and let you play it. What do I mean by all sources?
First, all your music, no matter what folder it’s stored in (except system ones like ~/Library or outside your home directory). Spotlight can instantly find all your music files no matter where they are stored, including in Dropbox, OneDrive or Google Drive. It will no longer irritate you with complaints about how it can’t find its files after you’ve reorganised them. This is how Picasa works — it shows you all your photos with zero administrivia or complaining.
Second, you’ll be able to use the new Music app as a library, by dragging music onto it to import it, after which you no longer have to manage the files on the filesystem or keep track of them or run the risk of accidentally deleting them. This is similar to how iTunes works today. Add your music to the Music app, and it will store them.
Third, the Music app will also find and play all the music you have in iCloud Drive, which is similar to Dropbox in that it lets you store whatever files and folders you want. The Music app will find all your music on iCloud Drive, whether or not it’s synced down to your Mac.
Fourth, there’s iTunes Match, which lets you upload  your music to the cloud and access it whenever you want. The Music app will let you play that as well.
Fifth is your purchase history on the iTunes store. Any albums or songs you’ve bought on iTunes will play in the Music app, without you having to download them.
Sixth are free Internet radio stations, and seventh, music subscription in the form of Apple Music.
Eighth is music stored on a connected iDevice.
iTunes today supports all these sources, but not very well. They’ll work seamlessly in the new Music app. You don’t have to worry about where it’s stored. It will find and play music from all these sources without any fuss.
The Music app will not only play music, but sync it to an iDevice for you. You can ask it to sync your entire music collection. Each genre, artist, album, playlist, etc will also have a checkbox for syncing. Tick this, and it syncs to your iDevice.
Or you can manage your iDevice manually. When you plug in your iDevice , it will appear as an icon on your desktop, like an external hard disc. You can then drag and drop supported files onto it from Finder. And folders containing such files. You can also drag genres, artists, albums, etc from the Music app to your iDevice.
iTunes today lets you drag and drop files and folders onto your iDevice, but that amounts to iTunes being a second-rate, ad-hoc file manager. If you’re going to be dragging and dropping individual files or folders onto your iDevice, there’s already an app for that: the Finder.
You can also double-click the iDevice icon on the desktop to see what’s stored in it. It’s presented as a virtual filesystem, with folders for different media types like Music and Videos. You can delete whatever you don’t want, or copy it back to your Mac. If you try to delete something synced from the Music app (via the checkbox I talked about above), it will warn that deleting it will turn off sync for the item in the Music app that caused the file being deleted to be copied onto the iDevice in the first place. That is, if I enable syncing for an album in the Music app, and then delete one of the songs from that album from my iDevice, it will warn that doing so will turn off sync for the album.
There will also be a folder for each app, into which you can drag and drop stuff to copy it back and forth. This is another case of iTunes acting as a crippled, awkward file manager.
When you right-click on the iDevice icon on your desktop, you’ll find options to upgrade iOS, restore a device, etc. This is again similar to formatting an external hard sic, and subsumes functionality currently in iTunes.
Moving away from the filesystem, there will also be a Videos app, which will work similar to the Music app. It will manage movies, TV series, documentaries, music videos , etc.
Instead of stuffing music and videos in the same app, separate apps will make it easy for users to find what they want. If you want to listen to music, open the Music app. If you want to watch a video, open the Videos app.
Having separate apps is also consistent with iOS. Why have the Mac be unnecessarily inconsistent? Having things in the Music app on the Mac sync to the Music app on the iDevice, and likewise for Videos, also solves the “Where did my stuff go? Which app should I open to access my synced media?” problem. If it was showing in the Music app on the Mac, it will show in the Music app on the iDevice. And likewise for Videos.
With this change, Apple can also get rid of QuickTime Player. The Music and Videos apps will work as standalone players: double-click an item in the Finder, and it will play either in the Music app or in the Videos app. And, since they track all your media even as they’re moved and renamed, you can easily find that item again to play. Or you can double-click it again from Finder or open it via Spotlight.
In summary, get rid of iTunes. Eliminate some functionality, like syncing contacts, calendars, etc to your Mac. Break the other functionality into two separate apps — Music and Videos app — and have a filesystem UI for manually managing files.
 A secondary reason is that iDevice users who use Windows (or Linux, for that matter) will want a web app. Apple has far more iOS users than Mac users, so even if every Mac user had an iPhone, the majority of iPhone users will probably be using it with Windows.
 Or match, but that’s an optimisation that doesn’t change anything.
 Or when it’s in Wifi range.
 It’s not clear whether music videos belong in the Music app or in the Videos app. Either choice will confuse users, so I guess the Videos app is as good a home for music videos as anything else.