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FlagSync is a synchronization and backup tool, which allows you to synchronize or backup your files with local folders (or an extern harddrive or flashdrive) and FTP-Servers, as well as synchronize your non-iPod MP3-Player with iTunes.
The source code is currently hosted at http://github.com/flagbug/FlagSync
Metadata Backup, originally written by Dale Preston, is a tool for backing up and restoring all the information in the Windows Media Player library, including ratings, play counts, and custom fields.
SubSet is a small file management tool that creates a random subset of files from a large collection and copies them to a target location. It is intended to fill a small MP3 player with random files from a much larger collection.
...It allows users to rename multiple files at once based on a list of regular expressions. Also allows batch editing of MP3 ID3 tags. Includes embedded Windows Media Player and picture viewer.
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If you create a playlist on a pc, you may want to listen to that playlist on a portable player. This copies the playlist and all files it refers to, preserving the dir tree. Use the gui or cli or create shortcuts to drop files on. M3U only for now.