Restore ipod playlists after crash

I have a 2nd gen 10gb ipod. I have a new 20" intel imac that I bought in January. I backed up my itunes library folder in January, before I bought my new imac. Two weeks ago my new imac's HD's firmware got corrupted during a windows re-installation attempt using bootcamp. The end result, I had to replace my imac's HD.
So... I dragged my backed up itunes folder into it's new place. It is two months old, but it resteored my music and album art from January. Problem is, I lost my playlists and two months of music that exists on my ipod which is current.
What is the best resolution/solution to make my imac and ipod be friends again and not lose data/music.

There are a number of third party utilities that you can use to retrieve music files and playlists from your iPod, this is just a selection. I use Senuti but have a look at the web pages and documentation for the others too, you'll find that they have varying degrees of functionality and some will transfer movies, videos, photos and games as well. You can also read reviews of some of them here: Wired News - Rescue Your Stranded Tunes
Senuti Mac Only
iPodRip Mac Only
iPodDisk PPC Mac Only (experimental version available for Intel Macs)
PodWorks Mac Only
PodView Mac Only
iPodAccess Mac & Windows
YamiPod Mac & Windows
Music Rescue Mac & Windows
iPodCopy Mac & Windows

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Restore ipod playlists after crash

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