Bug Terror! – iTunes (yep. again.)
Good christ. I mean, seriously, come on. I see the “Force Quit” window more than any other application in OS X. If Apple can’t allow users to sync their iPhones across at least two computers with iTunes (and without hacking xml files), then open it up and let users drag music to it like the iPod. It’s completely ridiculous. If there’s two things Apple cannot seem to get right it’s the integration of an external hard drive and their unwillingness to allow users to sync any of their peripheral hardware across more than one computer. In an effort to curb piracy, they make it so frustrating to work with files users have paid for that the alternative is much more inviting.
By the way, this is supposed to be a decent way of at least getting music and contacts synchronized. Good luck and enjoy that spinning beach-ball horseshit.

Oh yeah, and your “shuffle” sucks with more than 16GB of music.