Yeah, I have it crashing on something too. Super annoying.
Then I read about using Windows Media Player to sync your music, which can also be set to downsample it if you want to save space by taking 320kbs rips down to 192 or something more space-saving. However, today I'm having problems with WMP actually seeing all my music sitting in the music folder. No idea what that is about. Driving me NUTS.
I wonder if there is a good 3rd party sync app. I used to use one for the iPod ages ago that was way better than iTunes for sycning and organizing your music across multiple devices. But it has been years.