Used SyncITunes for Windows?
Developer’s Description
Do you have an iPod, but you don't like to use ITunes for managing your audio files? iTunes is the best software to syncronize your songs with iPod, but it's a poor solution to manage your songs. There are many better options. Before SynciTunes, you'd need to add your songs two times: In the software of your choice and in iTunes. Not anymore. This small application, with no initial setup, synchronizes audio files from a selected folder, including optionally its subfolders, in the iTunes library. SyncItunes renews the iTunes library from the selected folder.
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