moellenium, have you tried the checking the box for error correction in the iTunes import settings?
In 2005, when I first bought an iPod, I used iTunes with error correction to import all of my albums to AAC. It usually worked pretty well, but sometimes I would get artifacts in the files. Sometimes this was just because the disc was too damaged, but there were other occurrences when I would get artifacts in the iTunes rip, but when I tried it xAct, the rip would come out perfectly. So since then, I've used xAct exclusively. They may have improved the technology since then, but I have not used iTunes to rip in a long while, so I'm not up to date. However, as I've mentioned in my previous posts, the biggest issue for me switching from iTunes to xAct for ripping CDs is because of the iTunes music folder.