ITunes losing all music files imported since 6/2

I have a frustrating problem I can't seem to figure out. I am running iTunes 8.2 on Leopard 10.5.7 on an Intel iMac. I keep my music on an external hard drive connected by firewire 800.
The issue is that all of the new music I have added since 6/2 will not stay in the library. I will add the files which get synced to my iPhone and iPod without difficulty. At a certain point, when I go to sync, I will get the error message "The following songs could not be synced to the iPhone b/c they could not be found." This most recently occurred when I turned my computer on. These files are everything since that date. Nothing particular happened on 6/2. It's just that's the last album it has retained.
When I go to the library, all of the songs added since then have the dreaded ! next to them. The files are missing from my external hard drive, and from the back up of my external hard drive. They are not in the trash. Spotlight does not find them except for the copies in my emusic folder (which is fortunately where most of them came from so I don't have to re rip everything).
I have tried:
1. Reinstalling iTunes, including deleting some files from the library recommended in a different post (sorry do not remember which-- some plist files).
2. Running Disk Utility to verify and repair the external volume.
3. Reimporting the music and changing some metadata.
This has occurred with files I have ripped, purchased from the iTunes store, and imported from mp3s on my hard drive. It is incredibly annoying. Please help!
2. Reimporting the songs

Hey Georgia
The first link below will get you iTunes downloaded to your computer. Check your purchase history to download any previous purchase and the second article will assist with that. The final actable will assist with transferring any purchased content from your iPhone to your MacBook Air, anything that was not purchased will not transfer.
iTunes 11.1.2
http://support.apple.com/kb/dl1614
Downloading past purchases from the iTunes Store, App Store, and iBooks Store
http://support.apple.com/kb/ht2519
iTunes Store: Transferring purchases from your iOS device or iPod to a computer
http://support.apple.com/kb/ht1848
Regards,
-Norm G.

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