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This is what iTunes looks like when you connect your Shuffle.
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Synchronization Ease of Use (4.50)
You might think you know iTunes in and out, but unless you've owned a Shuffle, you might be surprised by this section. Typically you'd connect your iPod to your computer, iTunes would pop up, you'd select the device and go about customizing its sync options. While this is also what you do for the Shuffle, it has completely different sync options. You can opt to fill the device with random songs from your library, or sync over a playlist as per usual. You can also choose to have the Shuffle select higher-rated items more often than not, and whether or not you want each "autofill" to overwrite the current files. In all, the interface consists of a button, three check boxes, and a pulldown menu. It's hard to picture it getting much more easy to use.
Synchronization Features & Support (1.00)
Really, other than being able to automatically sync your files, there isn't much in the way of functionality here. Minimalism seems to be a recurring theme when dealing with the Shuffle.
Other Synchronization Software Features (8.00)
iTunes is software that, if you'll allow the metaphor, wears many hats. One hat lets it sync your music, one hat will play it back your music, and one hat will organize your music for you. Unlike when the typical human tries to wear three hats, however, iTunes has no problem wearing all three hats at once. If you like want sync software to be a multitasking, three-headed, magic-hat-wearing mostrosity, iTunes is for you.
As is the problem with any monster, if you aren't totally in compliance with it, you sometimes run into problems. For example, when you import a folder, iTunes will automatically convert your songs to AAC format. If you've stated you want to manage your own folders, then the new AAC file will just get dropped next to the file it was transcoded from. Now you have two different encodings of the same song. If you remove the folder from your library, but want to drop it back in later, it'll convert those initial songs again, meaning you now have three copies of the same song. The reason this is a problem, should it occur, is because iTunes doesn't have a good method for deleting duplicate files. Other programs, like Winamp, have a "delete duplicates" function. In spite of minor issues like this, iTunes is still the gold standard for synchronization software.
As of the newest update, iTunes also has Genius Playlists, but since they're functionally opposite of everything the Shuffle represents, we didn't award iTunes any points for the functionality.
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