So it appeaars that all my problems over the past month or so (ok computer problems) point to a bad 2tb hd in my rig. Dammit... This explains why iTunes has been a little pain in the butt as well as winamp freezing during my shows. I am using a back up drive for my music, and I am in the process of replacing the bad drive. The only issue I have is that sooooo many games are installed on the bad drive. Hopefully I will never want to play any of those games again.
This being said (knock on wood, Do it! I am waiting) I should be error free this Sunday. Of course I am now scrambling to make new play lists. Including a rock show.