Tried to sync new iPod and lost numerous purchased songs

The hard drive on my old 20GB iPod crashed and I finally replaced it today with a 30GB iPod video. I went to sync it with my computer, and I was making a new playlist, I noticed that some of the songs I had purchased back when I had my old iPod were gone. The majority of them are still around, but I lost probably 30-50 songs.
Anyone know why this happens or how to recover them? I am not particularly pleased with Apple right now (my first iPod lasted less than 18 months and the "Genius Bar" had no explanation for why the hard drive crashed and now this).

First, have you checked if there isnt some wierd authorization problem? Go to the Store tab in iTunes and reauthorize everything you use.
Also, something that has happened to me, is that for no particular reason several songs were dropped from my Purchased playlist. They were still in my music folder, they had just been deleted from the playlist.

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