Slightly different "dead hard drive" thread

I had my music folder in a secondary hard drive and on my iPod. My iTunes was installed on the primary hard drive. I lost my iPod (fell out of my pocket in a taxi, which drove off as I was trying to grab it) and then the secondary hard drive died. I now have a full installation of iTunes with all the playlists, songs, rankings, etc listed that I used to have, but iTunes' playlists all point to files that aren't there.
I had thought that since I had two copies of the files, I was OK for backup purposes (iPod Agent, etc), but I now have a copy of iTunes that lists over 700 purchased songs, and iTunes can't find any of them (since the hard drive is gone), and I can't restore them from my iPod (because that iPod quickly became a present to some cabbie's teenage daughter--hope she likes ska :-\ ). I've tried the basic home techniques to save the drive (including putting it in the freezer), but have had no success. Are my only options 1) repurchase of lost songs, and 2) professional data restoration?
If I have to repurchase the songs, is there any easier way than going through my old "purchased" playlist song by song? I don't really want to spend $700, but I really don't want to spend it one dollar at a time for my whole weekend...
And yes, I've since bought an big ol' external backup drive to prevent this happening in the future.
XP & Ubuntu   Windows XP  

Also:
If I'm not going to be tied to the .m4p's iPod exclusivity, is there any reason for me to pay for another iPod?

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