Richard Gabriel's "Worse Is Better" (1991) is always worth a re-visit.
It's a fairly succinct and technical reflection on why worse design design decisions often win. It also encapsulates why we're all using Unix and Windows running C code rather than more advanced and elegant Lisp machines.
He mentions ITS vs. Unix... which is a little funny because ITS itself was a hack of the "more correct" CTSS. https://en.wikipedia.org/wiki/Incompatible_Timesharing_System
@schmudde Darwinian fitness tests are rarely limited to any one idea of "best"
@evanwolf Yeah, I think he kind points to the same thing in his follow up article (https://www.dreamsongs.com/Files/worse-is-worse.pdf).
But the problem is that we (humans) are designers so these tradeoffs are difficult to foresee.
