I didn't downvote, but I would like to know the difference between an "Average User" and a "Somewhat Technical User" in the context of the StackOverflow community?
You're right that Stack Overflow appeals to a technical user. My point is that probably the majority of Stack Overflow users are not using microsoft tools and won't get the joke. A site like github manages to make a joke with their 404 and 500 pages that will likely resonate with the vast majority of their users, but even the ones that it doesn't won't be confused by it.
My point is that making a controlled outage look like dumped error code isn't wise if you're trying to appeal to a diverse crowd who might not get it.
I don't use Microsoft tools but I used my brain for a few seconds and figured it out. This sort of argument is why everything ends up so bland and boring. It's a site for programmers. Now we're worried about if certain programmers will "get it?". I know, lets just put a plain text 500 error page up since everyone "gets it".
My point is that making a controlled outage look like dumped error code isn't wise if you're trying to appeal to a diverse crowd who might not get it.