Hey all,
This is November, so here is a quick update 
We implemented the first three items listed above:
- docs.scala-lang.org/getting-started now covers both Scala 2 and Scala 3 on the same page
- The search bar is now available on every page of the Scala documentation website
- The navigation menu now allows quick access to more documentation pages (including tutorials, which were previously not listed).
I believe this has already significantly improved the state of the documentation website!
From my previous post, there is one remaining item, “consolidate the structure of the Scala 3 documentation”, which aims to organize better the content of the Scala 3 documentation. I realized that before I can start working on this item, we need to settle on the way the Scala 3 documentation website is produced. We are currently considering alternatives to Jekyll, with the benefits of a simpler setup (no need to install Ruby), the ability to produce documentation with interactive code examples, and the ability to maintain the source of the documentation in the same Git repository as the compiler implementation.
Last but not least, another very important point is to simplify the user experience from landing to https://scala-lang.org to actually having all the necessary tools set up to start programming in Scala. This task is addressed by the project Simplify the Getting Started experience with Coursier, roadmap.