For example, the author is complaining that Windows "forgot" his PNG file association, but I'm 99% sure this means that the author installed and then uninstalled some program that took the PNG file association, and Windows isn't designed to anticipate this kind of poweruser fickleness.
Likewise, the author is running their disk space down to <40GB free, and didn't think that this would cause problems (because to a poweruser, 40GB is like, so many config files!) A normal user who got into this situation would hand their PC to a slightly-more-technically-capable user who would notice that the disk was full. Or maybe they'd take it to a PC repair shop. But a poweruser spends "two days of debugging".