There's a old book all about just that, which included and popularized Richard P. Gabriel's paper, "The Rise of Worse Is Better":

https://en.wikipedia.org/wiki/The_UNIX-HATERS_Handbook

https://web.mit.edu/~simsong/www/ugh.pdf

>The year was 1987, and Michael Travers, a graduate student at the MIT Media Laboratory, was taking his first steps into the future. For years Travers had written large and beautiful programs at the console of his Symbolics Lisp Machine (affectionately known as a LispM), one of two stateof-the-art AI workstations at the Lab. But it was all coming to an end. In the interest of cost and efficiency, the Media Lab had decided to purge its LispMs. If Travers wanted to continue doing research at MIT, he discovered, he would have to use the Lab’s VAX mainframe.

>The VAX ran Unix.

>MIT has a long tradition of mailing lists devoted to particular operating systems. These are lists for systems hackers, such as ITS-LOVERS, which was organized for programmers and users of the MIT Artificial Intelligence Laboratory’s Incompatible Timesharing System. These lists are for experts, for people who can—and have—written their own operating systems. Michael Travers decided to create a new list. He called it UNIXHATERS:

    Date: Thu, 1 Oct 87 13:13:41 EDT
    From: Michael Travers <mt>
    To: UNIX-HATERS
    Subject: Welcome to UNIX-HATERS

    In the tradition of TWENEX-HATERS, a mailing list for surly folk
    who have difficulty accepting the latest in operating system technology.
    If you are not in fact a Unix hater, let me know and I’ll remove you.
    Please add other people you think need emotional outlets for their
    frustration.

https://www.amazon.com/UNIX-Haters-Handbook-UNIX-Haters-line...

https://www.goodreads.com/en/book/show/174904.The_UNIX_Hater...

https://wiki.c2.com/?TheUnixHatersHandbook

>I'm a UnixLover, but I love this book because I thought it was hysterically funny. Many of the war stories are similar to experiences I've had myself, even if they're often flawed as a critique of Unix itself for one reason or another. But other UnixLovers I've loaned the book to found it annoying rather than funny, so YMMV.

>BTW the core group of contributors to this book were more Symbolics Lisp Machine fans than ITS or Windows fans. ITS had certain technical features superior to Unix, such as PCLSRing as mentioned in WorseIsBetter, but having used it a bit myself, I can't see that ITS was superior to Unix across the board. The Lisp Machine on the other hand, although I never used it, was by all accounts a very sophisticated environment for programmers. -- DougMerritt

https://news.ycombinator.com/item?id=13781815

https://news.ycombinator.com/item?id=19416485

>mtraven on March 18, 2019 | next [–]

>I founded the mailing list the book was based on. These days I say, Unix went from being the worst operating system available, to being the best operating system available, without getting appreciably better. (which may not be entirely accurate, but don't flame me).

>And still miss my Lisp Machine. It's not that Unix is really that bad, it's that it has a certain model of computer use which has crowded out the more ambitious visions which were still alive in the 70s and 80s.

>Much as the web (the Unix of hypertext) crowded out the more ambitious visions of what computational media for intellectual work could be (see the work of Doug Engelbart and Ted Nelson). That's a bigger tragedy IMO. Unix, eh, it's good enough, but the shittiness of the web makes humanity stupider than we should be, at a time when we can ill afford it.

https://medium.com/@donhopkins/the-x-windows-disaster-128d39...

Shameless plug: You could buy a copy of the book! ;)

https://www.amazon.com/UNIX-Haters-Handbook-UNIX-Haters-line...

Or just download the pdf file:

https://web.mit.edu/~simsong/www/ugh.pdf