I think they don't always communicate well with industry practitioners, and your reactions are great evidence of that.
Racket is lead by professors, and (as is sometimes the case in systems research) some of them are very highly skilled software developers, well above HN average. But they have not been working in industry, and some have never worked in industry, so they don't always know what notes to hit, and they don't always know current subtleties of practice.
My best example of this is when someone kept saying the platform was "batteries included". My reaction was, my god, no, please don't say that: the first time the wrong person sees that, invests time with that expectation, and finds all the ways that is absolutely not true by industry convention, they will rip the ecosystem a new one.
Set expectations properly, and you attract the right people, who will love it, and they will also disproportionately be great programmers.
That said, the software engineering quality situation is much better than the impression you seem to have. They've done a very solid job of rehosting Racket internals, and of generally maintaining backward-compatibility over the years. Much better than Python, for example. (Also, Racket docs are usually much better than most ecosystems I have used in recent years.)