Daxx,
That's a mess, but one of the features added via the many iTunes updates over the years is the ability to back-up your library (database files, and actual music/video content) to CD/DVD. I backed up recently, and it took (8) 8GB dual-layer DVDs ⚠, and about 6 hours). As they say, files should NOT considered to be backed up, unless they exist in 2 other locations on two other types of media (I back-up my library, which is on ext HD, to another HD; now it's backed up on DVD).
Even though I'm not sure how well the process worked (burn errors on some files 5 hours into the process), it saved my bacon when the library files on HD were overwritten afterwards. Fortunately, I was able to recreate the library when I replaced the database files on my ext HD with those I just burned to DVD.
So if nothing else, it's a good idea to back-up the iTunes DATABASE files (iTunes Library, iTunes Library.xml, and iTunes Music Library.xml) periodically, because my understanding is iTunes doesn't allow the user to recreate those files without manually re-adding the music files. You also can back-up the PAID apps/music only, which saves some time (free podcasts can generally be downloaded again, but interesting to note older podcasts are not available).
Guess I'm saying, my library had gotten disorganized and fragmented over the years (e.g. I had files living inside sub-files, due to years of updates that changed file structures and user errors (e.g. I had RAM go bad a few years ago, which can introduce HD write errors). And there were times the ext HD had not been mounted and iTunes used another back-up drive, etc).
I needed to sort it out: Apple cannot back-up files for us, as that remains the responsibility of the USER.
And sorry, but it's not possible to advance the OS X platform for the benefit of the majority of users without leaving the "stragglers" behind (I gave my PB G4 17" (with 10.4.11) to the kids, who'll not need the latest/greatest advances of OS X just for homework, e-mail, browsing, etc).
The competition (e.g. Windows 7) and chip-makers have moved on to more powerful 64-bit processors and OS, and Apple couldn't NOT adapt to changes without the perception of falling behind.