You can use iTunes to copy to your iPod but not to copy them back to your hard drive. I don’t know if this has been intentional to please the Music Industry but I doubt it was just an error that could not be corrected in later revisions of iTunes. You have to look elsewhere if you want to copy songs from the iPod to a hard drive again, lucky for us tools that can do this exist and are free to download and use.
A freeware that can copy songs from an iPod is iDump for example. It consists of only an executable file that can be run from your computer or from the iPod directly. Just copy it to the main directory of your iPod and run it from there. You probably have to enable disk mode in iTunes to be able to see the iPod as a drive in Windows. The freeware compiles a list of all the songs on your iPod and displays a list of them in its main window.
You may select all or only some files in the main window. All important information are displayed: Title, Artist and Album and iDump makes it possible to sort the list using those information. To copy songs from your iPod you need to specify a directory where you want to copy the songs to and select a file output format or choose the default one.
Other options are mandatory like creating a playlist from all copied songs or using unattended transfer options which handle the case automatically if a file in the destination directory already exists.
The software is available for Microsoft Windows XP, ME and 2000 and works with all iPod generations including the latest iPod Video and iPod Nano.
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I guess that it is rather stupid for Apple to do that. People should have the freedom to do what they pleased with the ‘goods’ that they have purchased, such as songs or video files.
someday other mp3/mp4 players will surpased Apple’s ipod…