The Unix model is a mess, the WOSA is a mess, personal computing hardware is a stack of hacks, programming environments are a poorly integrated mess, software 'engineering' is still back in the age of siege engineering rather than modern engineering discipline, and emacs still takes ages to boot.
Computers are marvelous productivity and life-enhancement tools, but following the easy path has led to stagnation in the mainstream.
I wonder though, is reckless advancement better than taking time to do it right? A lot of people are finding success with the fail-and-iterate model -- isn't that essentially what we've identified as a problem now?
There's a good reason for this, which is backwards compatibility, in terms of concepts, education, maintaining a skilled workforce, and retaining the value of prior investments in hardware and software.