On a similar approach, I created and actively developed from 2014 to 2019 Grafoscopio, which, while being inside Pharo and a companion of all other tools, was providing a computable outliner to do something: write computable and reproducible documents and bridge the gap between the IDE and the app for a more mature audience (a similar approach for children was previously tested in Squeak, with Etoys).

This allowed me to write the Grafoscopio Manual (2016) inside Grafoscopio or to do with the community some hacktivist republishing, like we did with the Data Journalism Handbook (2018)

Of course, being those initiatives from the so called "Global South" and being Grafoscopio my first "real program" ever, they lacked the visibility of Global North initiatives, like the ones you collected in Smart Academic Notebook, but they were acknowledge and appreciated in small/specialized communities, like the Pharo community.

With the new GUI/DX provided by Lepiter (2021), I have been migrating the Grafoscopio Lessons from the previous half decade to this technology, with the MiniDocs package and I imagine Grafoscopio becoming more a software distribution on top of Pharo/GT, providing documentation and collaboration workflows and improved outlining with packages like TiddlyWikiPharo or the Brea decoupled CMS / static site generator.

BTW, as I don't know how to add comments or suggest updates I wonder why this note is not updated with Lepiter as it provides pretty much the experience you were advocating for since 2018 and it is already in your wiki/bliki. Maybe it is just a matter of some wiki refactoring a links update.