Yes--poorly understood and documented requirements also cost agencies millions. But I do make a distinction there--those problems are caused by people highly expert in their domains but not in systems design, while MS's update decisions are made by people who should know better.
The problem is the motivations for clarity:
1. The OS developers are paid for maximizing features and minimizing the cost to deliver them. They have every incentive to cut corners with their verification processes and configuration management.
2. Users have come to expect that OSes will change and ruin their systems no matter what they do, so they are not rewarded for being clear about their requirements--things are going to change out from under them anyway.
I think Floyd Toole would call this the circle of confusion
The result is a lot of economic inefficiency. MS's lowered costs are more than offset by the user's higher costs for testing (if they are able to do that) and accommodation of new OS changes, including eventually just giving up and buying new systems rather than sustaining the current system. I see this as being the case at all scales of systems that use PC networks that share operating environments with consumer systems. But avoiding that and going with specialized systems has the opposite problem--enhancements soon become unmanageable and unaffordable because there is no general market support for the product pool.
From a marketing point of view, many of the changes are motivated by marketing to new customers rather than sustaining the requirements of old customers, who the OS companies take for granted.
Linux is actually a reaction to this, but only by those capable of sustaining that reaction. That means that only professional software people (and dedicated hobbyists) can contribute and keep up. This is the problem I have with Unraid, even though it totally fulfills my requirements as a product. When a new OS update comes out that breaks my access to my Unraid server, questions to the Unraid forum, which I visit only when I need such help, usually result in advice I cannot use, because I am not a pro in that field. I have to decode highly coded instructions full of jargon and abbreviations that assume a floor a knowledge far above my ceiling, and that forces me to spend days just catching up to the advice before I can even implement it. I'd rather have a turnkey system. But no turnkey system on the market so clearly fulfills my requirements for backup storage.
But I can also no longer get my Win10 computer to see network shares on a Win7 computer in my home network. I go in and allow SMB v.1 and make a few other changes, and the computer appears for a while. But then tomorrow it's gone again, even though those settings I changes still show as being changed. So, I edit them again and it appears again, only to disappear soon after. I'm sure it's an easy fix to a pro. But that's the nature of my complaint--things that used to be easy, like moving files back and forth between several computers in my home LAN, are now difficult or impossible for production users (i.e., domain experts who have user needs, not systems experts who are supposed to fulfill the requirements emerging from those needs).
Most people just buy new stuff every two or three years and throw their old stuff in the landfill, and then they feel good about making their local government require that grocery stores charge (me) for the use of plastic bags or whatever because they are so environmentally conscious. Good environmental sustainability means sustaining hardware for it's working life, not replacing it every few years because it has simply become too hard for it to support the latest bloatware.
The problem for me is that my desktop computer needs serious power to do the photo editing I use that computer to do. Being expected to replace it every two or three years just to keep supporting features I neither requested nor want just pisses me off. My system is surrounded by expensive hardware that can't be replaced at all in some cases, and getting the computer to support that hardware is difficult enough as it is. My $3000 Nikon film scanner is irreplaceable and needs firewire, for example. My $3000 (to replace) Eizo monitor is old but highly effective with full hardware calibration and color management and build quality that cheaper models don't have. The Unraid server is just the current issue I'm fighting.
The surrounding hardware in my professional work is even more demanding and expensive.
Rick "wondering how much monstrously expensive hardware is sustained by individuals willing to curate their own computer museum" Denney