I think you're conflating cargo culting with pragmatism though. The generalized reason that everything is messy is because it's too much work to gather all the knowledge and consider all the angles and do a big reset, and even when you do, you run into unforeseen issues that may end up being just as bad (see Gall's Law).
Consider a pet peeve of mine: The Turkish Problem. Specifically, when Turkish was latinized almost a century ago, they had the brilliant idea to use lowercase i and capital I as separate letters, and then introduce their counterparts İ and ı as new letters. This now means you can't upcase or downcase the letter i/I unless you know the language. Note that it took 11 years for Firefox to handle this correctly (https://bugzilla.mozilla.org/show_bug.cgi?id=231162), and even then you have fractal complexity if you're dealing with an internationalized site. I had the pleasure of working on a film site that was localized to Turkish, where I realized that it is not enough to know the language of the document, you must indeed know the language of every string in the site. In the case of film titles for instance, many films in Turkey are known by their English title, and in that case you must use normal capitalization rules, so now every film title has to have the original language flagged. This is not a small issue because if you are a Turkish speaker it just looks wrong if you don't get it right.
Why do I go into this digression? Because from a programmers perspective, this is insane. In retrospect it would have been infinitely better just to invent a new letter or use an accent or something that fit the alphabetical semantics of other latin languages. But they didn't. This decision went into effect in 1929 when the concept of character encodings was something only maybe a handful of engineers and mathematicians had even considered, and the concept of Unicode would have been beyond science fiction; it probably seemed a perfectly reasonable hack at the time. If we were to reverse it now in order to ease technical concerns think about all the fallout with all the existing documents and printed materials. It's just too big a price to pay. The world is full of these things, there's just not a big enough ROI to justify overhauling these old systems.
That's very different from the more actionable problem of people who go through the motions without ever questioning how they do things.