If things are this broken for people who live and breath all this stuff, imagine how broken it is for the average Joe who doesn't have the skill or confidence to understand why software sucks.
The average Joe/Jane doesn't run into this stuff because the average Joe/Jane doesn't have quite the volume of email that Scott does. Nor do they have the enormous social graph that Scott does.
I'm not going to whitewash his entire point by saying he's an edge case, because some of the problems he points out aren't a problem of scale. Some of them, like Chrome 19 and VS, I can't reproduce. Which means nothing and is the exact reason Google and Microsoft will give him for not fixing the problem.
The question for Scott and others is: Has software gotten WORSE? Or does software just suck in different ways?