You're totally right that you have to know your audience and cater to it. Technical writing still requires it. What changed my perspective though is the book "

You're totally right that you have to know your audience and cater to it. Technical writing still requires it. What changed my perspective though is the book "Comedy Writing Secrets". It's a very different topic, but the general aspects of writing fun an engaging texts translate quite well. One example I've seen it done brilliantly is the re-frame docs https://day8.github.io/re-frame/re-frame/ https://day8.github.io/re-frame/re-frame/ - I often point it to people as an example of technical writing so good, that its fun to read just for the sheer pleasure of it, regardless of whether one writes Clojure or not. _why's (Poignant) Guide to Ruby is also a famous example of this.