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MacOS Mojave (e.g. 10.14 from 2018) ruined font rendering on standard DPI screens, which included every single Macbook Air from before that year (the first 'Retina' Macbook Air was released in 2018.)

A Catalina update completely broke Thunderbolt docks, causing kernel panics every other time you connected one.

(Seems like it got better in Big Sur, and haven't had a single one in Monterey)

macOS 10.15.6 had a showstopper kernel zpool memory leak if you used virtualization software to run windows VMs, requiring multiple reboots per day in order to stay in place. It was an absolute dealbreaker for productivity as a developer who needed windows vms.

Agreed, if anything minor updates have been either transparent or visibly addressing issues. I have had some problems when updating from major macOs version to another though. Windows unfortunately has the tendency to break even with minor updates regularly. It is so much of an issue that we have a process at work to test those updates on a few machines and roll them widely to the remaining after.