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Synchronization Ease of Use (7.50)
Synchronizing your Nano is done exclusively through iTunes. iTunes will sync over your music by playlists, so if you want to sync over your whole library, you'll have dump all your songs into a playlist to sync them all over. A nice feature of iTunes is its dynamically-changing playlists, which will let you sync over your top rated, recently added, recently played, and top 25 most played songs, keeping them separate from all other files.
iTunes, like most things from Apple, is intuitive and has a very small learning curve. You choose what playlists you want to sync over by first selecting your device from the list on the left. From there, you can select the music, photos, podcasts, or video tab. On the music tab, you select the specific playlists you want the device to synchronize with. For the rest, you select the folder you want to sync up with, with a filtering criteria (you can select specific podcasts, or opt to only sync over unwatched TV episodes).
Synchronization Features & Support (5.00)
The Nano does not support wireless synchronization, so you'll need to use the proprietary USB cord included in the box. The Nano will show up as a removable hard drive and let you use drag & drop tactics to get any non-media files onto the device. For media files, it's either iTunes or unliscensed thrid-party workarounds. Regardless of what you end up using, this dependency on software is a bit annoying. Further, if you do end up using iTunes, your device can only synchronize with one copy at a time. This means you can't put songs on your Nano at home then pull them off at work (without evil third-party software, that is). This is Apple's way of preventing rampant music piracy, but it's really more annoying than anything else.
Providing you're willing to play by iTunes's rules, it's a good piece of synchronization software. You simply drag & drop files into your iTunes library and iTunes will automatically convert the files into a usable format and set about finding the album art. You can also use iTunes to sync over your contacts or calendar info. It should be noted, however, that you cannot edit this data on the device.
Other Synchronization Software Features (9.00)
iTunes is sync software, a media player, a music organizer, and a store all rolled into one. Providing you tell iTunes to do so, it'll keep track of your music for you. If you edit a song that's incorrectly tagged, iTunes will automatically drop it in the appropriate folder and keep track of it for you. This is great functionality. If you don't want iTunes to organize your music for you, however, you will run into problems. First of all, if you have files that iTunes first has to convert, it'll drop the converted file into the same folder as the original. If you remove the song from your library and add it again, iTunes will again offer to convert the song for you, resulting in duplicate AAC files and duplicates in your iTunes library. While iTunes thankfully comes with a "View all duplicates" filter, you still have to manually go through the duplicates deleting every other one.
As of the newest update, iTunes and the iPod Nano support Genius Playlists. These playlist files are either generated by iTunes or on the device, and generate playlists based on songs it thinks go together. This is great functionality, and helps to heal the Pandora-shaped hole in each of our hearts.
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