I always thought one of the most interesting insights into this was the Unix Haters Handbook
https://web.mit.edu/~simsong/www/ugh.pdf especially Dennis Richie's anti forward:
The systems you remember so fondly (TOPS-20, ITS, Multics, Lisp Machine, Cedar/Mesa, the Dorado) are not just out to pasture, they are fertilizing it from below.
Your judgments are not keen, they are intoxicated by metaphor. In the Preface you suffer first from heat, lice, and malnourishment, then become prisoners in a Gulag. In Chapter 1 you are in turn infected by a virus, racked by drug addiction, and addled by puffiness of the genome.
Yet your prison without coherent design continues to imprison you. How can this be, if it has no strong places? The rational prisoner exploits the weak places, creates order from chaos: instead, collectives like the FSF vindicate their jailers by building cells almost compatible with the existing ones, albeit with more features. The journalist with three undergraduate degrees from MIT, the researcher at Microsoft, and the senior scientist at Apple might volunteer a few words about the regulations of the prisons to which they have been transferred.