OK, I lied about going to bed. I just saw that CNET.com has the easy tutorial on retrieving music from a Windows iPod that I have always been meaning to write since discovering my music in the hidden iPod_Control\Music folder. Someone finally beat me to it. Oh well. And yes, it’s just as easy as the tutorial shows.
What the tutorial fails to mention is that the music files have truncated filenames. That is, it only shows the first ten or so characters IIRC of the filename, then it mangles it with a ‘~’ or something. The trick to getting it back with a proper filename is to use a file renamer that can look into the ID3 tags or let iTunes (or any other music library software) organize/rename your music files. The advantage of iTunes organizing your library is that it also quickly separates the files into folders by artist and album title.
Also, the music files on a Windows iPod are marked as hidden files. This isn’t normally a problem, but if it is, you can just unhide the files. If you use the file properties dialog box, there is a checkbox on the General tab to mark the file(s) as hidden. If you feel like venturing into the command line, you can always run attrib -H «path to music folder» /S /D. This will unhide all the files and folders contained in the music folder you enter.
That is all good. But is there a way to rename the files to their ID3 Tag titles and sort acccording to the albums they belong to automatically?
The easiest way to have the files renamed and sorted is to tell iTunes that you want it to organize your music automatically. In the iTunes options, go to the General tab under the Advanced tab. Check the box next to "Keep iTunes Music folder organized.". I also turned on the option "Copy files to iTUnes Music folder when adding to library." When you add your files from the iPod to iTunes, they should get copied into your iTunes Music folder, and also get renamed.