ITunes deleting music at random? or maybe not so random?!?!

okay, so for the past few months i have had some suspicion that some of my mp3s where missing. i have about 100gb of music on my PC. two things have happened: first, not all my music shows up on iTunes.
I have iTunes manage my folders, but some folders seem to disappear off the list and I have to drag them back in. that's a small thing, here is what bothers me.
I noticed some of my mp3s are missing. I have a mix of mp3s: some purchased (not from the iTunes store), most ripped from my CD collection, an some downloaded (Limewire, Kazaa, etc). the mp3s that I know for sure I had came from the CDs that I ripped.
I spoke to my bother who has about as many mp3s on iTunes as I do but hosted on a Mac. he noticed that some of his mp3s have gone missing to. To be clear: I have checked the iTunes folder, and searched all my other drives, the are COMPLETELY gone!
has anyone else had this problem? is this a rights management thing, a software thing, or what? any insight would be greatly appreciated!

This is not a common problem from the posts I have seen. There are certainly complaints of Libraries (or songs) gone missing, but many times, that can be chalked up to some fumbled instructions given to iTunes by the user (no offense intended).
If you have lost both the song references within iTunes and the song files on the PC, then several things had to happen:
- The song reference got deleted from the iTunes Library
- The song file got deleted from the PC's HD folder
- The song file got emptied from the Recycle Bin
These actions do not usually occur without some action by the user. For all three to occur would more than likely need some further action on your part. That, or the elimination of the iTunes dialog boxes that ask for confirmation of a reference deletion or sending the song to the Recycle Bin. Do you still receive these warnings when deleting a reference or file from the Library?
Do you examine your Recycle Bin prior to emptying it? Are you sure? Especially if/when there are many files in the Bin?
Do you seem to receive an inordinate amount of broken links ('!') within your iTunes Library? This may indicate that the PC music files are being relocated, deleted or changed (file name) outside of iTunes.
Do you repeatedly ‘Rebuild’ your Library from the underlying PC song files? Do you periodically change the location of the main Library Folder within the iTunes Preferences?
Do you actively run a backup program for your massive Library? Can that program indicate when incremental backup are required due to changes? In either direction (source vs. target / target vs. source)? This would also help you to quickly identify when some unwanted changes have transpired and may lead to an investigation to uncover the root cause.
Unfortunately, without much more information and inspection from you, there just is not enough to go on for a diagnosis of your underlying problem(s).
What other commonalities can you observe and communicate? While there may be some 'Ghosts in the machine', many problems are usually traced back to user actions that had unintended consequences. Once known, they can be prevented, or at least explained.
BTW: With over 12,000 references within my iTunes Library, I have never had a PC song file 'go missing'. I've had some mysterious broken links show up due to the file names being changed (but not by me - really) that I cannot fully explain (I do have a theory). I have kept a very close eye on my Library and PC files as a matter of course, but that's just my inherent mistrust of any computer file management system.
Above all - keep several backup copies of your Library: music files and iTunes database index.

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iPhone, iPad, iPod touch: Device not recognized in iTunes for Mac OS X
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ITunes deleting music at random? or maybe not so random?!?!

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