Yes and no. Some of the struggles are fresher than others, and in some cases you do internalize things to the point they feel like a second nature.

The effort mentioned here of getting newer people to read the content and/or produce it is something I've done a lot in the past, and one of the ways I've used in on-boarding people as well. We (the co-authors of Adopting Erlang) tend to do it with topics where we don't know everything the other authors know, and provide feedback to each other about things that lack clarity.

I've also taught Erlang stuff in multiple places and started knowing some of the things people find confusing as a kind of pattern, which may get easier to address early on with time.

The thing that can never be done well, though, is predicting the things someone with an entirely different background from yours would find confusing; the context carried by their experience influences the things they understand and the information they extract from a text. Teaching to a functional programmer is different from teaching to a developer who has done OO their entire career. Teaching to someone doing front-end work is going to be a different experience from teaching to someone doing mobile or back-end work. The same may often extend to sociological, economical, or cultural factors as well.

All of this means that each teaching experience has new surprises as well and you can't just cover them by thinking very hard. Frequent reviews, both technical and from editors can help, though, along with your own experience when teaching.

No. What you're describing is the problem people have when teaching/providing insight/responding to questions online. They all use their current understanding and apply it to the question not assuming the other person has no knowledge of the subject.

Haven't you ever seen someone ask a question online that had a "newbie" answer that is generally correct, only to have a ton of people flood your response with all the caveats ignoring who their audience actually is. The default for most people is to use your current knowledge.

This struggle is often referred to as the "Curse of Knowledge"

https://en.wikipedia.org/wiki/Curse_of_knowledge

Becoming familiar with a system makes you forget what was and what was not obvious. I experience this with myself. Once I've learned something well, then I can find it hard to explain it to someone else. I find it best if I write down assumptions that got corrected or unclear things as I encounter them.

I've seen this in other disciplines, and if anything to worse degree. I've witnessed situations where the old masters can't talk to the journeymen, and the new masters can barely talk to the beginners. You learn by watching and whatever the people a couple years ahead of you can decipher for you.

To make matters worse, what often happens is that the instructors believe they have taught something, and they don't witness the actual learning take place, so they continue in their belief in their practices.

As someone who did a lot of professional training and love to teach complete beginners it’s definitely possible but it’s not intuitive and it’s a lot of conscious work.