Was a bit skeptical. But it works. iPodTrans shows you all of the files on your iPod. GUI is organized. Kind of hard to tell what action to take since the actions aren't designed as buttons. They're simple text links. Selecting songs was easy (as long as you know how to use SHIFT, CMD etc).
After hitting "copy selected" songs...there is no indication that something is being copied. Nor, that it is successful, completed or failed. That would be nice to have.
After I got the files to a test folder on desktop, I double clicked a file (files get copied to your harddrive with names like EIRPDK.mp3 etc.)
BUT once you play the song in iTunes the song gets added to your iTunes library with the correct filename (usually the title of the song).
1. Create a folder on your desktop to copy the selected songs into. The filenames will be useless since they are just a bunch of letters and a file extension.
2. Then drag them into your iTunes app. Make sure that the "Copy Songs Added to My iTunes folder" is selected in iTunes>Preferences AND "Keep my iTunes folder organized" is checked.
Doublecheck your iTunes music folder after adding them to the iTunes app and you'll find that the files, albums and artist information is all intact.
Great product despite the small GUI/HCI shortcomings.