At this point, I'm not sure it's worth investigating. This isn't the 90s when everyone was running application software directly on their PC; now everything is done in the cloud or through your web browser somehow. I honestly find it funny when Windows users have all kinds of agony because of that "contempt" you refer to; if they don't like it, they're free to switch to another OS. I've been watching this for over 25 years now but people just won't give up Windows, even when they only use it for web browsing, so I've lost all sympathy for them, even though the Windows user experience keeps getting worse.
windows is/was laden with malware, requiring antivirus, just full of crap for decades.
Now in the DMA/DSA times, things are different. It took them a couple of decades, but the EU is starting to take action.