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Windows 7. Some may say 8.1 if they were willing to tolerate it, but most will agree that Win7 was the last “true” OS that wasn’t riddled with adware and telemetry collection.
Microsoft lost a lot of money on Win8 (and by extension, 8.1). That made them rethink their business model, and they shifted away from selling the OS. Instead, they gave the OS away and made money on the data collection. Because Win8 made them realize that the world didn’t want or need a new OS every other year.
It’s the same reason people don’t upgrade their cell phones every year anymore. At first, the hardware changes were meaningful, and you actually got large upgrades with every new iteration. You were noticeably behind if you had a phone that was two or three years old. But now that modern hardware design has slowed down, (and hardware changes are more akin to updates on existing hardware), people don’t feel like they’re behind if they put off upgrading for two or three years.
And this reluctance to upgrade hardware meant people and businesses weren’t constantly buying a new OS every year. So Microsoft lost a lot of money when Win8 launched and everyone collectively went “actually, I’m good with my current computer.”
One another factor is hardware manufacturers started to screech at them to make Windows even cheaper for them, because Android is technically free (save for the driver licenses) in exchange for user data collection, so they started to kneel.
I'd go as far as Windows 2000. This new XP crap is too shiny, and why did they hide the controls?
The same is happening with Windows 11 as well. People don't want to upgrade to it. With its pervasive adware and information gathering. The only reason the company I work for is buying Windows 11, is that you can't buy Windows 10 anymore.
Phones can have exponential growth in hardware capabilities, but the bigger thing is they don't need to get more powerful.
All the app makers want their apps to work on any device, so a 10yo budget phone with 1/60th the horsepower of a modern flagship will work just fine with most apps, and New phones are just way overpowered for what they actually do.