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Rockbox
I found out the hard way that the library file has to be updated by iTunes, you can't just put the files in the iTunes library and expect them to show up in iTunes.
:: Options::::: /r Do subdirectories.:: /a Add new media to iTunes database.:: /t Update iTunes track info from ID3 tags.:: /c Clean orphaned entries out of iTunes database:: /x Close iTunes after update.:: /e:"<strings>" File extensions, separated by spaces, e.g. ".mp3 .m4a .m4p".:: /db:"<file>" Location of iTunes database file."C:\Program Files\iTunes Library Updater\ITLUconsole.exe" /r /a /t /c /x /e:".mp3" /db:"C:\Documents and Settings\Jim\My Documents\My Music\iTunes\iTunes Music Library.xml" \\Audrey\F\mp3
dbPoweramp will maintain all the artist/album/track info IF the original flac files are tagged properly. I just ran a test with 164 tracks from various folders from flac to mp3 and had no problems. But if the tags are not complete then it will not work out well.
DBPoweramp's Batch Converter is the greatest. Just pick any number of folders or songs, pick a destination folder, and voila. It does NOT delete the original set of files (that would be a bad design). It can also filter format types just in case you have LAC among other formats and only want to convert FLAc (to say, MP3). I've converted over 500 songs at a time, no problem. You can even maintain same folder heirarchy if you want (I think that capability requires a Premium version).
--waiting for the 64 gig ipod touch so I can switch from the ipod video.