One of my current peeves is just how much time we spend maintaining and upgrading computer operating systems, even as ordinary users. The workload for this is unacceptably high, though it's not as though people are unaware of the problem.
Right now I'm updating one system to the beta of the new Ubuntu Feisty Fawn. (Ubuntu is the Linux distro I currently recommend.) They have done some work on building a single upgrader, which is good, but I was shocked to see an old problem resurface. In a 2 hour upgrade process, it asked me questions it didn't need to ask me, and worse, it asked them at different times in the process.