tl;dr What should you do?
First, I’m moderately aggressive in applying updates across a variety of systems and I’ve not had any problems.
Second, look at Woody Leonard’s post on ComputerWorld. There’s some hyperbole there but overall not bad advice.
So here’s the background…
Microsoft has had a bad month with Windows 10. They’ve had problems with Display Audio issues (jpeg), file deletions (archive.is), HP keyboard (archive.is), and most recently audio problems (archive.is).
I’m not going to rehash all these problems but Microsoft has to step up to the situation that they have 700,000,000 Windows 10 users. That’s a lot of zeroes!
One of the response to the above problems was that it only affected “one one-hundredth of one percent of version 1809 installs.” If that had rolled out to the entire population that would have been 70,000 users.
When I was at FedEx, I heard Fred Smith speak a number of times. One time he talked about the “Golden Package.” His point was that we (the FedEx employees) couldn’t let the numbers mask the impact of every service failure.
Fred instituted a Service Quality Indicator (SQI) system where service failures were measured not by percentages but by the count of failures. It didn’t matter that a given failure was a minuscule percent of service. Each service failure got reported, researched and counted against our performance objectives.
That made a difference as the number of nightly packages skyrocketed.
Maybe Microsoft needs to take a similar tact.