IPod won't play songs that were lost on my PC from drive crash

In January my hard drive crashed (Win2000) and I lost all the music on my PC. NO big deal, replaced the hard drive and restored my CD's, figured I could just play my purchased music from my iPod.
the problem is that SOME (not all) of my purchased music now won't play on my iPod even though the songs are physically there ... this started after iTunes 6 came out ... but different songs seem to play on different dates ... it is very weird. Today I sorted by "date added" and discovered that anything purchased between 6/22/05 (my birthday, coincidentally or not?) and 12/31/05 will not play on the iPod ... UNLESS I had copied the song to a CD and restored to my hard drive from the CD.
Songs that I have purchased since replacing the hard drive worked for a while, then wouldnt' work, but I could delete the song from my iPod and re-copy from my PC. Obviously this won't work for all the music that I lost though!
Music from this account is authorized for 4 devices so that isn't the problem, any suggestions?
Thanks!

If you have made sure that both the iTunes and iPod software are current and have deauthorized and reauthorized your computer, try this:
1. Deauthorize the computer.
2. Create a new user in the system.
3. Download the free song of the week from the iTMS in the new user account.
4. Play the song in that user account to authorize again.
5. Restore the iPod (using the iPod updater) in the new user account.
6. Sync just the free song of the week and see if it plays on the iPod.
If it does, you appear to have a corrupted iTunes library file, and you should recreate the iTunes library file in your normal user account, and then sync your music back to the iPod and all should be well.
The following articles will help you.
Authorization and Deauthorization.
How to create a new user account in Windows.
How to restore the iPod.
How to recreate your iTunes library.
"Music from this account is authorized for 4 devices"
Not sure what you mean by "devices". It's computers that are authorized for purchased music not iPods/

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