I've had luck with several scripts and freeware downloads used to transfer a few songs or an album to a Mac drive, but I finally wanted to back-up the entire content of my 40GB iPod to an external hard drive.

iPod->Folder allowed me to transfer 99.7% (9,303 songs out of 9,330), when others left me missing anywhere from hundreds to even over a thousand songs.

It does often truncate the file names in the transfer process, but the song titles and proper info appear correct in the iTunes window.

Besides, in iTunes under "Preferences" - "Advanced", I clicked the boxes marked "Copy files to iTunes Music folder when adding to library" and "Keep iTunes Music folder organized". This duplicates the files into folders based on artist/album and seems to return their original file names.