> but overall it reads like a typical transition from thinking static typing is a burden to realizing type safety can be incredibly useful.

I got this impression too, I was just like the Author in that I hated static type checking as a Junior, but as I gained more experience it flipped from "I hate this" to "this is the first thing I implement in a new project".

To your point of thinking that newer languages being "better" than older ones. I think that also comes down to experience. At first I thought the same way, but the most experience I gained the more I realized that each language is a specialized tool for using in specific cases, some tools are very very specialized (WASM for example) while others are broad (like Javascript).