"Choose boring technology" implies many different things. I don't like this phrasing because it doesn't identify what part of "boring" is important:
* Is boring tech good because older tech with lots of commits is more likely to have identified bugs?
* Is boring tech good because it is easier to find devs with skills in those areas?
* Is boring tech good because it has lots of fleshed out examples to follow/SO support/packages?
* Is boring tech good because it is simpler and has less moving parts?
Simply saying "Postgres" or "JVM" doesn't imply boring either. Both of these have lots of advanced features and complexity. Your interactions need to be boring (simple, avoiding advanced features). Moreover it's very powerful to make your application boring. What if your whole app could only read/write data in one place? What if your whole app could be single threaded rather than multi-threaded (and still deliver results)? There are good reasons not to do these things, but those cases are rarer than the times we jump to these solutions which can create difficult problems that make our lives harder later
I agree with you and would even go a bit further. Actually the word "boring" is completely misused in my opinion. It is all about choosing the right solution. This has nothing to do with things being boring or fancy. The word boring is clearly defined by a dictionaries and is subject to personal emotions. One could say the JVM is totally amazing while the other says it is dull and boring. This can not be the basis for an educated decision.
The points you mentioned are also part of the questions one has to ask for finding a suitable approach.
I think that all those who say "use boring ..." effectively want to say something else but either do not dare to do so or are otherwise unable to express their intentions. Nevertheless redefining the word "boring" is not a solution.
The essay makes it fairly clear to me. There is a constant churn of fads in the tech world. Usually they are beneficial for some specific use cases, but get hyped up beyond all belief until everyone wants to use the new tech without questioning whether they should or not. If there aren't ton's of articles about how great a new tech is then it's probably "boring". Think of it more in terms of fashion than interesting.
* Is boring tech good because older tech with lots of commits is more likely to have identified bugs?
* Is boring tech good because it is easier to find devs with skills in those areas?
* Is boring tech good because it has lots of fleshed out examples to follow/SO support/packages?
* Is boring tech good because it is simpler and has less moving parts?
Simply saying "Postgres" or "JVM" doesn't imply boring either. Both of these have lots of advanced features and complexity. Your interactions need to be boring (simple, avoiding advanced features). Moreover it's very powerful to make your application boring. What if your whole app could only read/write data in one place? What if your whole app could be single threaded rather than multi-threaded (and still deliver results)? There are good reasons not to do these things, but those cases are rarer than the times we jump to these solutions which can create difficult problems that make our lives harder later