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> those small, quick-to-make dynamic codebases ended up becoming unmaintainable monstrosities

In my experience, type checking / type hinting already starts to pay off when more than one person is working on an even small-ish code base. Just because it helps you keep in mind what comes/goes to the other guy's code.

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And in my experience "me 3 months later" counts as a whole second developer that needs accommodating. The only time I appreciate not having to think about types is on code that I know I will never, ever come back to—stuff like a one off bash script.

> "me 3 months later" counts as a whole second developer

A fairly incompetent one, in my experience. And don't even get me started on "me 3 months ago", that guy's even worse.

"How has that shit ever worked?"

Me, looking at code 100% written by me last year.

It gets worse with age and size of the project. I’m getting the same vibes, but for code written by me last month.

Yep, I've seen type hinting even be helpful without a type checker in python. Just as a way for devs to tell each other what they intend on passing. Even when a small percent of the hints are incorrect, having those hints there can still pay off.

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