One of the features that's missing on iTunes is the ability to extract the songs on your iPod. Floola allows you to do this and much more.
Use Floola to manage all the multimedia information stored on your iPod, from songs and their lyrics, to the podcasts or videos you download from YouTube.
You can also use Floola to manage your playlists, locate duplicate or lost files, convert file formats that aren't supported by iPod, and export its contents to an HTML file.
x
If Floola asks you for the iPod FWID, you will find it as the 'Serial Number' in the Apple menu -> About this Mac -> More Info -> Hardware -> USB -> iPod

Floola iPod and Floola Desktop are now available (version 2012r1)!
Floola is a freeware application to efficiently manage your iPod or your Motorola mobile phone (any model supporting iTunes except iPhone, iPod touch and nano 6G).
Floola Desktop is another freeware application to manage your local PC music library.
Both are standalone applications that do not need installation and run under Linux (any GTK2 distro), Mac OS X (10.4 or newer!) and Windows (98 or newer, including Windows 7).
Features:
Floola supports almost all features offered by iPods including photos, artwork, podcasts and smart playlists!
It automatically converts any incompatible audio or video file so that you can copy almost any file to it. It allows adding youtube and myspace videos with a single click. Now it even makes it possible to keep your Google calendars synched!
Take a look at the feature list to find out what it can do and feel free to suggest anything that might be missing.
Cross plattform
Works on any Windows (98 and above), any Mac and any linux distribution with GTK installed.
Portable
Put the application on iPod and launch it on any PC, immediately.
Copy
add and extract songs to and from iPod.
Playlists
Easily manage, import and export (m3u, pls) playlists.
Last.fm
Join the social music revolution.
Podcasts
Join the social music revolution.
Web videos
add files to iPod just copying the page url
Localization
Available in different languages.
Lyrics
Lyric support even on older iPods (3G and above).
Search for duplicates
Easily find duplicated songs on iPod.
Search lost files
Easily find songs lost in your iPod.
Artwork
Add artwork to your songs easily.
Videos
Videos can be added to iPod.
Convert
Convert audio and video incompatible formats
Google Calendars
Synchronize them easily
Export to HTML
Create HTML files containing list of your iPod files
Fix iPod
Did a software mess up your iPod? Fix it!
Notes
Manage notes.
Growl support
(Mac version only) Get beautiful system notifications.
Snarl support
(Windows version only) Get beautiful system notifications.
Music
Play iPod's music.
Photos
Freedom to simply add photos to iPod.