Another problem is when people explicitly try to do a simplified explanation, most seem to be unable to extract the essential concepts from all the implementation details and end up writing massive walls of text in which every technical term is explained further using everyday analogies.

You see this a lot on reddit's /r/explainlikeimfive, but the best example I've seen is the answers here: https://security.stackexchange.com/questions/55343/how-to-ex... - with the top-voted XKCD cartoon as a counterexample.