> Why is it broken by design?
I think your example self-explains why it's broken by design. It's a good example.
> a command line interface must be human readable and machine readable at the same time. There is no canonical way to solve this problem.
And you know, there could be one. Apple has Human Interface Guidelines to reify the meaning of the visual abstractions in its desktop UI. The problem is that the command line didn't come from people who think like Apple designers; it came from people who think "How can I express what I want using the least code possible, because laziness, impatience, and hubris are virtues?" And they weren't wrong for the time (especially because every byte matters), but the design decisions they made got baked into tooling that can't now be moved.
I think at this point we'd have to punt the POSIX toolchain to get something better; it's hard for me to imagine how we'd build discoverable, conceptually-consistent UX atop what we currently have.