Those were on windows with about 600 gig music and its painful. Really I have just stopped moving much music because of this reason, plus I only have windows on an older machine I don't use much. Last time I tried to use it under virtual box on ubuntu it didn't work at all because of USB issues.
I find that all the mac users I know are always waiting on the next update to fix some sort of problem. As an example, one of my friends cannot connect to a bluetooth network due to some bug that was introduced 2 years ago.
It's too bad you can't go in there and, you know, jumble some plumbing around and get it fixed.