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Pro Can create a playlist based on rules
There is a feature included in iTunes called Smart Playlists that allows the user to create playlists based on criteria such as BPM, Genre, Artist, Album, Plays, Rating, etc.
Pro Can automatically create playlists based on a chosen song
There is a feature called Genius included in iTunes that allows the user to select a song and create a playlist based on that song. It will analyze the music library and choose songs similar in tone to the one chosen.
Pro Syncs across devices
Synchronization of playback information, podcast subscriptions, and settings is possible in iTunes. It can also automatically download purchases made on other devices.
Pro Airplay support
Streaming audio to all Airplay enabled devices within WiFi range is permitted by iTunes. It's also possible to select more than one device to play a song at the same time.
Pro Can auto-import CDs
The user can set up iTunes in such a way that media (from CDs) can be automatically imported once a CD is inserted. This also comes with customizable import settings (bitrate, codec). Additionally, iTunes can automatically fetch track names from the Internet.
Pro Built-in parental controls
iTunes parental controls can be used to deny access to certain parts of iTunes such as podcasts, internet radio, store, or shared libraries, as well as restricting access to media that has a certain rating or warnings.
Pro Can autopull information about songs
Track names and album artwork can be automatically obtained by iTunes.
Pro Sleek interface
The interface of iTunes presents a flat, clean design with playback controls at the top-left, search at the top-right, and a row of ways to categorize available media beneath that. It can also be minimized to take up much less space. The minimized interface is called the Mini Player and it can be set to display on top of all other windows. It's possible to show iTunes on top of all other windows when playing movies as well.
Pro iTunes store has a huge selection of media
The iTunes store offers a huge catalog of videos, songs, and podcasts.
Pro Advanced podcast management
Pro iCloud integration
Pro Internet radio
A music streaming service called Radio is available in iTunes. It creates stations based on chosen genres, songs, or artists and requires Apple ID for access.
Pro Ability to add RSS feeds
The ability to add RSS feeds in iTunes keeps the user informed of the latest web content.
With each update, iTunes appears to get bigger and bigger, though adding little more value, especially for the user who just wants to listen to and organize music.
Con Buggy iTunes app
Immediately after the worldwide launch of Apple Music, a new version of iTunes was released (12.2). Many users have reported issues with this release, such as music lists getting mixed up, music having wrong metadata, etc.
Con Unfortunately required to fully manage iPods
Con Duplicates media files
Con Album organization can be fragmented
Songs purchased from the same album at different times will be added as separate albums.