Right, it's important to keep "worse is better" in mind, but also keep in mind that the philosophy fades in importance the longer that a technology has been around. For instance:

"C is a programming language designed for writing Unix, and it was designed using the New Jersey approach. C is therefore a language for which it is easy to write a decent compiler"

Is that still true? Over time, people have wanted to fix the flaws in C, so they have added features, and nowadays writing a compiler for C is less easy.

And there are other ways to measure the declining value of "worse is better." Many people would now argue that memory safety is worth the extra effort. Many would say the world would be a better place if C was banned and everyone switched to something like Rust. C continues to lose market share to those languages that guarantee memory safety, and yet C never fully dies, which is interesting.

Over time, the tax you must pay for the "worse" begins to cost more than what you gain from the simplicity. My point, above, was how long this can take. We think of the tech industry as fast moving, and yet many core technologies have had obvious flaws for 30 or 40 years, and yet little action is taken to move to better technologies.