Back when I fixed computers for the public I used to see a lot of badly organized iTunes libraries. Part of the problem was duff data from Gracenote/CDDB or whatever provider they use. Double albums and compilations were the most problematic, since apparently at the time no-one could agree on a format for tagging those. If course if you bought your music from Apple it was okay, but most people had lots of CDs to rip. Apparently most users didn't know how to fix the problems either.
iTunes was fine if you used it for everything - ripping, buying and syncing. If you wanted to do any of those things with another app though...
... you had to do EVERY FUCKING THING YOURSELF. Which is obviously what you want because you are anal - but smarter people use a program like iTunes for that.
I giggle every time I see an apple purist claiming that they are "smarter" people. I'm sorry, itunes is horrible.
Work continues in this area. -- DEC's SPR-Answering-Automaton