The type systems of Java and C/C++ are the most commonly encountered ones and by far the most widespread in industry programming (as opposed to academia/research) and they are actually awful and really add a lot of friction and inertia to developing. Being free of that kind of type system when using a language like Python really does feel like a big upgrade.

There is a different problem with the more powerful and useful type systems in more modern statically typed languages though: learning curve. Haskell is dysfunctionally hard to learn and other languages do a little bit better but there's still friction in the learning curve that gets in the way of widespread adoption in projects that want to be able to hire rapidly.