Exporting a listing of songs

Unfortunately I have to get a new iPod because my current 5th Generation broke. It no longer plays sound, and as I've discovered through another thread this is becoming quite common in the 5th Gens. However, I know that there are songs that I don't have the files for on my current PC. I had downloaded some songs on my old archaic PC, and unfortunately as that PC started to come close to its inevitable demise I couldn't back up files.
So my question is, is there a way that I can sort of export a listing of files currently on my iPod so that I can compare that list with my present Library on my PC and see what I will need to purchase again? In addition I would need to know how I could export that same listing for my iTunes library. Preferably I'd like an Excel format. As an Accounting geek I know how I can compare these two lists rather quickly.
Thanks!
Kelly

*is there a way that I can sort of export a listing of files currently on my iPod so that I can compare that list with my present Library on my PC and see what I will need to purchase again*
You can copy the songs themselves from your iPod to your computer. The transfer of purchased content from the iPod to authorised computers was introduced with iTunes 7. You'll find details in this article: Copying iTunes Store purchases from your iPod or iPhone to a computer
The transfer of content from sources such as songs imported from CD is designed by default to be one way from iTunes to iPod. However there are a number of third party utilities that you can use to retrieve the music files and playlists from your iPod. You'll find that they have varying degrees of functionality and some will transfer movies, videos, photos, podcasts and games as well. Have a look at the web pages and documentation, this is just a small selection of what's available, they are generally quite straightforward. You can read reviews and comparisons of some of them here:
Wired News - Rescue Your Stranded Tunes
Comparison of iPod managers
TuneJack Windows Only (iPhone and iPod Touch compatible)
iPod2PC Windows Only
iDump Windows Only
SharePod Windows Only
iPodRip Mac & Windows
YamiPod Mac and Windows
Music Rescue Mac & Windows
Floola Mac & Windows
iGadget Mac & Windows (iPhone and iPod Touch compatible)
iRepo Mac & Windows (iPhone and iPod Touch compatible)
iPod Access Mac & Windows (iPhone and iPod Touch compatible)
TouchCopy Mac & Windows (iPhone and iPod Touch compatible - Windows version only)
There's also a manual method of copying songs from your iPod to a Mac or PC. The procedure is a bit involved and won't recover playlists but if you're interested it's available on page 2 at this link: Copying Content from your iPod to your Computer - The Definitive Guide

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