Great blog post discussing how Remacs' design has evolved: https://shanavas.org/rust/2017/11/08/remacs-the-journey-so-far.html
Related Posts
I'm a huge fan of Swift's 'Error Handling Rationale' design document: https://github.com/swiftlang/swift/blob/9315673c003875158852579bd1f33480cdec5461/docs/ErrorHandlingRationale.md#fundamentals
It carefully defines terminology and compares with other languages, so you can understand Swift's position and preference in the design space.
Exploring design ideas using AI as a learning assistant, for creative exploration: https://andymatuschak.org/hmwl/
@krinkle A surprising number of PL design workarounds are "just add another equals sign" 🙃