I've also got two 30GB drives but am running the same root playlist (shuffle and no-shuffle) procedure without a problem. I've got just under 5900 tracks, so that may be your problem.

Then again, your problem may be one or two problem tracks. Try this:

Make two root-level lists, each with half your tracks. Now play each, one at a time to see if either hang. Of course if they both hang then it gets trickier. You'd then do another binrary division, but make the split somewhere else. Or divide into four lists, etc.

Bruno