Syncing iPod w/ iTunes with reinstalled OS

I just reinstalled my OS (again) and now my iPod will not sync. It gives me the option of erasing my iPod or transfering my purchases. I am using the latest updates of iTunes and OS X. Some of the songs on my iPod are no longer on my computer because my computer crashed and I lost a good third of my music library (I know I should have it backed up!).
TIA
Rob

"I just reinstalled my OS (again) and now my iPod will not sync. It gives me the option of erasing my iPod or transfering my purchases"
Actually it will sync, that's the point of the message you are getting. However it will erase and sync so you just need to be careful connecting if your iTunes is empty or hasn't got the same content as the iPod. Connect your iPod and when you get the message that it is linked to a different library and asking if you want to link to this one and replace all your songs etc, press "Cancel". Pressing "Erase and Sync" will irretrievably remove all songs from your iPod. Your iPod should appear in the iTunes source list from where you can change the update setting to manual and use your iPod without the risk of accidentally erasing it. Check the "manually manage music and videos" box in Summary then press the Apply button: Managing content manually on iPod
Once you are safely connected instructions on how you can transfer any purchased content back using iTunes can be found in this article: Transfer iTunes Store purchases using iPod
The transfer of non iTMS content 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 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
PodWorks Mac Only
PodView Mac Only
iPodAccess Mac & Windows
YamiPod Mac & Windows
PodUtil Mac & Windows
iPodCopy Mac & Windows
Keep your iPod in manual mode until you have reloaded your iTunes and you are happy with your playlists etc then it will be safe to return it auto-sync again. I would also advise that you get yourself an external hard drive and back your stuff up in case you have problems again. External drives are comparatively inexpensive these days and you can get loads of storage for a reasonable outlay.

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http://discussions.apple.com/message.jspa?messageID=818692#818692
http://discussions.apple.com/message.jspa?messageID=607582
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and this, as well: http://ottodestruct.com/itunes/RemoveDeadTracks.txt (right-click, save-link-as)
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https://discussions.apple.com/thread/2452022?start=0&tstart=0
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