ITunes, what have you done with my files?

Question

Irrelevant backstory;
I've actually had quite a turbulent time with technology lately- External harddrives blowing up, iTouch screens cracking in my pocket. Not to mention the screen on this ruddy Mac of mine. But I'm fairly competent with technology and so far have been able to fix most problems I've made for myself. This one is a little tougher so I'd really appreciate a little help.
This is a long story, mostly because information tends to yield better solutions. Feel free to skip to the short version below if you'd like to save your eyes the trouble.
Essentially, I replaced my iTouch yesterday. This 9 month old beauty had accumulated thousands of listens, and since it was manually managed from itunes Last.fm refused to scrobble any of them. So I made my mind up that I'd simply sync the new one automatically. That's when things started to go wrong. I had deleted all my music from the harddrive for the purpose of downloading fresh films, confident in the fact I had two recently backed up external harddrives containing all my music (about 3,000 songs I like, and 1,000 songs other people like that they give out to me for not having) and movies. Altogether, this came to around 24 GB. I realise this is not a huge amount in comparison to what some people have, but I'm a relative purist (except when drunk) and some of the music is exceptionally hard to find (ever heard of Ween?). So I'd really like it back. Now, as I've mentioned, one of the harddrives is a glorified paperweight, it fell 3 feet and is now making typically awful beeping/scratching noises and no longer fires up. The second one was working fine, however, so I plugged it in and set to work copying and pasting.
iTunes duly realised that none of the music was where it used to be, so I re-added my C:/Music folder to the library and got plenty of awesome duplicates. After deleting those, iTunes would play the song if I tried to click on it (exclamation point or not). Problem sorted then, except that because iTunes didn't realise it knew the locations of the songs once more, virtually none of those songs were synching with my spanking new iTouch. So I started manually clicking into the exclamated songs, which would play, and the sync. I got halfway through A before realising this would take forever. So I searched for a more automatic way. I tried readding all my songs again, but this just created tons more duplicates, and after deleting those went into the File->Library->Organise Library menu. Things go badly for me from here.
I knew what Consolidate would do and I didn't like it. I could guess what Reorganise would do, but hey, it might help, and it specifically said it wouldn't remove or delete any files. Just move them.
So I figured what the ****.. Why not?
Mistake.
After taking ages to reorganise my already organised music folders, iTunes promptly lost around 1500 songs. Individual songs and albums. It seems everything that wasn't a Compilation from Kings of Leon-Come Around Sundown (of which I now have half an album) was gone. So I resigned myself to locating the songs manually.
But they weren't there. The first 7 songs were there from Come Around Sundown. The remaining ones were not. I thought this pretty odd. Then i noticed that the rest of the songs weren't there either. Alphabetically, from "K" down, most of my music was simply not there. And I now had this funky new C:/Music/Music folder, which was just full off the songs I did have. After tinkering around with the XP search function and finding nothing anywhere, I decided to simply delete and start over. So I wiped my Music folder and recopied everything from the external HD. Re-opened the folder in iTunes and voila, everything was the exact same.
My only thought here is that I've managed to wipe the Music folder in the external HD, and replaced my wanted music with what iTunes has done to my laptop. Highly stupid, absolutely, but not absolutely out of character with deleting the music in the first place, or reorganising my music folder despite misgivings about it's effectiveness. In fact, it was par for the course with how I approached this problem last night.
Short version;
iTunes has, apparently while reorganising my library, deleted a number of songs from my computer. I now have far less music than I should, and it is not anywhere on my computer. The music folder has shrunk from 24GB to 16GB. My movies have been renamed into oblivion. This was not what I thought reorganising did.
Reorganising = File->Library->Organise Library->Reorganise files in the folder "Music"
"Music" is my music folder, containing all of my beloved tracks. It's located at C:/Music
What's interesting now is that when the iTouch synched with iTunes, it did manage to pick up all of my movies, despite them not being there. When the iTouch is plugged into iTunes and i look at the Movies tab (close to Summary on the top), everything is there. When I look at the Movies viewer on the left (below Music) it's empty. I tried to manually sync some movies to save space (plus, I've already watched Team America a dozen times now) it removed all of them. They will no longer go back on, but iTunes does show them in the Movies tab.
They're still there in theory, but neither a manual search for them nor allowing Movies to sync automatically puts them back onto the iPod touch.
Solution wise, I'm stumped. If the computer doesn't let me find them, then they're not there. But Reorganise expressly pointed out that files would be moved and renamed, not deleted. And the Music folder has shrunk in size, which indicates that iTunes was lying. The only ways out I can see are to a) attempt to repair the damaged hard drive which contains all my unharmed music or b) acquire all my missing music again.
Option a isn't bad, since I'd like to get that HDD working again anyway. Option b is going to take a long time and will be incomplete. Folks, after all this text what I really want to know is- Anyone got an option c?
Cheers! And apologies for the length. I tend to ramble.
~SFD
iTunes is fully up to date. The iTouch software is 4.3.2 instead of 4.3.3, but internet is expensive so downloading that update will not be done on Telstra wireless. The laptop is a dualbooted MBP running XP.

Answer 1

tl:dr?
Really?
There was a short version expressly for people who weren't bothered to read a myriad of text.
Meh, not that it matters anymore. I ended up redownloading 70-odd albums, so I have the bulk of my music back. And I still have no idea what iTunes did with my files, but I'll make sure it never does it again.
I would thank you for the help but you were utterly useless. Oh well, carry on.