My pre-retirement last job was with a very large US industrial company (several hundred thousand employees, multiple divisions, worldwide footprint). We did MANY tests before going to new OS versions. We entirely skipped several major Windows updates due to programs that would not properly run, including Windows 8 (worst I've ever seen).
About 20 years ago, I read thru all of the patches included in cumulative periodic updates to Windows (usually about 1500 - 3000 corrections listed). This was similar to a readme file. A lot of the problems that reach end-users are due to other corrective measures that are made last minute, but are slammed in, seemingly without a full cycle of tests. I've never seen a good sized update to any OS that didn't result in at least a few problems where many third party and custom applications are in use.
Not every third party software or hardware is going to work with an OS. It is the responsibility of the software provider to meet the specifications of the OS. Similarly, if you modify a car/truck with third party parts and one of those parts damages the vehicle, it can void your warranty (you are responsible for damage to expensive electronic or mechanical parts). Most people don't read what you agree to when installing an OS or third party application (most just click the OK button). Many of these agreements limit your ability to collect damages, and specify a number of types of applications that will not be covered in the event of a fatal or serious injury. Sometimes, there can be a lot of finger pointing between the OS vendor and third party vendors (or in-house developers). Sometimes the third party must disclose their code for examination, and may need to pay a fee for corrections to their code to meet standards. I've had to supply programs and data to an OS provider, and several third party software providers in the past (but have never been charged a fee, other than normal software support fees, usually in the thousands to a hundred thousand dollars). Corporate paid several yearly fees, at least one in the millions per year to Microsoft and a few other companies.