Can't offer you much advice, but wanted to let you know I'm in pretty much exactly the same boat. Owned a Creative NJB3 for a year plus. When it failed, I sent it back to Creative and was charged $150 for a fix. It suffered another failure just weeks later (out of warranty for the repair, of course), and, frustrated, I bought an iRiver iHP-140, which, like you, I have recently decided just isn't worth it due to the problems you describe (although check out Redchair's iRivium (or Notmad) software for organization). For me, the interface is the biggie, and I just like the Creative UI better. I'm now debating a 60 gig Xtra or a 40 gig Touch. But I am still very hesitant to trust Creative again... When did you have your Xtra(s)? I know that they have made some attempt to fix the headphone problem in more recent batches of the player...