(See below for explanation.)

• Add docs/README.md as documentation index; link to it from README.md and CONTRIBUTING.md ("Further Documentation") (Add a docs directory #16579)
• Split MAINTAINERS.md into docs/maintainers.md (maintainers list) and docs/maintainer-guide.md (information for maintainers); integrate some information from CONTRIBUTING.md
• Rework/review README.md
• Rework/review MAINTAINERS.md
• Rework/review CONTRIBUTING.md
  • Split metadata documentation into own file; keep brief description and required fields
• Rework/review tests/README.md
• Rework/review tests/REGRESSION.md
• Rework/review stdlib/_typeshed/README.md
• Add a "stub conventions" documents; should mostly refer to Writing and Maintaining Stub Files, but include our own additional guidelines
  • Add DSL policy (i.e. how we annotation object.__eq__ and other base methods that may be used by DSLs in non-standard ways)

Over the years typeshed has accumulated a lot of documentation. Most of it is still useful, but it could be better structured to help new users, experienced users, and maintainers alike to find the information they are looking for. For example, probably the worst "offender" is our contributing document. This is mainly a document for new users (and should ideally be read in its entirety), but contains a lot of arcane information, for example about the intricacies of the METADATA.toml format. It doesn't help that every change will create a popup "contributing has changed" for every user when creating a PR.

The list above is just a bunch of initial ideas I have, and is by no means complete or set in stone. I've also written "review/rework" for basically every existing document. This doesn't mean that all documents need changes, but we should at least have a look at them to confirm that.

I've also created a new label "project: documentation" exclusively for documentation-related issues and PRs.

I'm not sure that I can dedicate how much time I can dedicate to this myself in the foreseeable, but I wanted to at least write down my current ideas and have a "hub" to refer back to later.