I mean, yeah. Casey mentioned in his video this downfall started around 1995-1996 with the whole advent of "plug and play". Windows XP would be a part of that, but a large reason why people don't recall Windows XP release bugs and problems is because those problems were not problems for the general population of users. They were problems that largely affected businesses, colleges, etc, just like you described. I know of no one personally who was affected by any of the worms in the early 2000s. But even in that case, many people (most especially corporate companies) tend to not to adopt new operating systems quickly. They were not updating to Windows XP on day one. It doesn't excuse the issues, but it does make them less relevant because you're not put into a position where you're forced to update.
In 2017, over half of the businesses in this country still relied on at least one system that still ran Windows XP. TODAY, over 15% of all PCs still run Windows 7. If I recall, over 90% of all banking ATMs still run Windows XP to this day. If software is so much better today, why are they doing this?
How many people are running a year old version of Chrome? Are you allowed to even do that or does it FORCE update you? I have an Adobe CC subscription for my business, and this thing automatically updates itself multiple times a year to add its new bloated bullshit and there's nothing I can do about this. Oh sure, I can turn off auto updates, but the moment I need any level of support whatsoever they aren't going to touch this unless I'm on the latest version.
Speaking of photoshop, with the latest update, I can't even figure out how to save a generic Windows BMP anymore. They removed almost all file types supported by save as, and you can't export many images as a BMP either, even with RGB color space and 8 bit depth. If you search online, no one seems to have a clear answer to this yet.
Fucking terrible experience, because I need to be able to save 2048x2048 BMPs the old way, and there's no clear way I can go back to an older version of photoshop that lets me do this.