Both PSPWare (http://www.nullriver.com/index/products/pspware; $15 USD) and iPSP (http://ipsp.kaisakura.com/; $19.99 USD)two of the more popular media managers for the PSPoffer automatic syncing of music to the PSP, using a playlist of your choosing from your iTunes Music Library. This is great if you use iTunes, but if you prefer to use different music managing software on your computer, these two solutions may not be ideal.
Again, keep in mind: these tools will only be able to manage iTunes playlists containing MP3s or AAC files that are DRM-free and have had their file extensions changed to .MP4.
Again, keep in mind: these tools will only be able to manage iTunes playlists containing MP3s or AAC files that are DRM-free and have had their file extensions changed to .MP4.
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