To rephrase what I mean: I disagree with the idea that we can explain all technical concepts in non-technical way, which OP seems to support. I don't think we can get much better with teaching monads than providing actual formal definition plus motivating examples. I simply believe monad is too abstract and we can't have a nice analogy similar to the one OP provides ("Functors can be broadly explained in terms of containers..."). In my opinion the "platonic ideal of a monad tutorial" is more or less the (semi) formal definition of monad + some motivating examples. This is also something that cannot be understood if you don't have proper background (which is understanding simpler typeclasses like monoid and functor).
I also would not call monads a pain point to be fair.
I would turn that on its head: Provide several motivating examples, together with concrete solutions. Once you've provided a couple of those, then you can call attention to the commonalities that unite all those solutions. At which point, the abstract explanation is almost trivial.
For example: My understanding of monads ultimately came together rather quickly and painlessly. After I had initially just given up on the whole thing. And then I watched Scott Wlaschin's Railway Oriented Programming talk (https://fsharpforfunandprofit.com/rop/). And then I learned what's really going on with LINQ's query DSL and SelectMany. And had someone show me how to easily compose Optional types without having to forever be explicitly interrogating whether they have a value or not. With all that under my belt, the pattern suddenly became rather obvious.
What did not help me in any way was any article that explicitly sets out to try and explain monads. They are all, as far as I'm aware, guilty of tring to sow the seeds before tilling the earth.
It was quite similar for me. Scott Wlaschin's Railway Oriented Programming and its other articles on its site (and in particular https://fsharpforfunandprofit.com/series/map-and-bind-and-ap...) helped me greatly too. I liked its idea of an "elevated world". Another helpful source was/is https://wiki.haskell.org/All_About_Monads. But I thought a lot about them for the past few years. I tried also to make a detour through category theory but it did not help except for getting a lot of books in my library.
I also would not call monads a pain point to be fair.