The last two releases of iTunes (and weren't they rapid fire!) seemed to have a problem with my iPod. And I write seemed because it's difficult to tell: all iTunes would tell me was that it couldn't sync my iPod because “An unknown error occurred (–50)”. (This is iTunes on Windows XP. I use iTunes on Windows mostly for historical reasons—I had ripped my CD collection to that machine before I had a Mac.) With the last iTunes in the 5.x line, it would inform me of the error, and then carry on regardless (which is interesting behaviour), so I just ignored it. After updating to 6.0, evidently error number –50 became more serious, as it wouldn't sync at all. So I was forced to do something about it.
I checked the software on the iPod itself—it was the latest version. Being in Windows-mode, where the standard second-line solution to every problem is re-installation, I figured I'd just wipe the iPod and re-install the music from the PC. It worked, but it wasn't very satisfying.
Really bad error reporting seems to be a standard Apple software trait. Why is that?