He says that he learned to read around 1990, and just about remembers navigating computers in the mid-1990s and using them in the early noughties -- the 2000s.

So, earliest OS Win95, learning to use them WinXP.

That is the beginning of enshittification. Windows 3 is when the GUI came to the PC, but it's also the beginning of the era of PCs crashing all the time. It's also the beginning of the era of dial-up internet, meaning patches from online, meaning it was OK to ship bugs.

The previous generation of PC software was the height of the DOS era. Lightning-fast apps like WordPerfect, sold on their speed and their device support. If a printer could put marks on paper, WordPerfect would drive it, and drive it as well as it could be driven. Hacks like overprinting twice for bold, backspacing the print head and typing underscores for underlining.

People navigated documents by just pressing the cursor-up or cursor-down key and waiting: the text blurred into a flickering wall of grey as the text scrolled much too fast to read, but with skill and practice, you spotted the shape of the paragraph edges to spot where you where and let go, and it was tuned to stop instantly.

Computers were shipped with 1 app and used in that single app for years, sometimes for decades. Walls of floppy disk cases, thousands of media, hand indexed.

Speadsheets tuned to be no bigger than fit in RAM, and used daily for years on end, upgraded only for faster recalcs.

Home computers with libraries of tens of thousands of games, and not a single byte of update or bugfix in playable lifetimes of years, because there was no way to distribute updates, so you made sure it worked as shipped. Tiny playable imperfections became cheat modes.

In offices, multiuser boxes running OSes like Concurrent CP/M or, if you were richer, SCO Xenix, or for big corporations, OpenVMS, with uptimes in years. Operators who used apps 7-8 hours a day for a decade and who could navigate with keystrokes so fast that a CRT couldn't update quick enough to show the UI in time for their controls... and developers knew this and detected the keystrokes first and acted on them, and updated the display later when there was time.

Giant mainframes running hundreds of thousands of lines of code in 1960s languages, arcane and hard to modify, so they are still there 50 or 60 years later, buried under layers of terminal emulation and screen-scraping so now they look pretty. Still running natively on modern gigahertz-class bespoke CPUs today and every time you use a credit card or book an airline flight, it goes through that half-century old code.

Those enterprise minicomputers had clustering Linux will only ever dream of, with individual running processes able to migrated seamlessly from node to node across different CPU architectures, while in use. Cluster uptimes in decades. Still running today. OpenVMS is still being maintained, still running. So are all those IBM mainframe OSes.

Ever seen Tron? The big baddy is MCP, the Master Control Program. That was a real OS, an old fashioned one in 1982 when Tron was made.

It is still maintained. You can still buy it.

https://www.unisys.com/product-info-sheet/ecs/clearpath-mast...

It was released 65 years ago and there is a current version on sale. It was in production 8 years before Ritchie and Thompson typed the first line of UNIX into a terminal on their PDP-7.

Sure, it looks like it has got better, but only if you entered this world right at its lowest point. Before that lowpoint, before Microsoft subsumed the world in a second-rate copy of the best of the 1980s, SOFTWARE WAS BETTER.