SLF, engineer and ex-college teacher here.
Based on the NYT article, it appears Boeing has "technical pilots" who write checklists, manuals and instructional materials. But the accountants at Boeing barred these "technical pilots" at Boeing from flying (did they keep their licenses current?) and so the "technical pilots" based the Max instruction manuals they wrote on the NG-derived sims, which of course do not evidence the significant force necessary to manually trim using the small NG trim wheels, especially at speed.
This is going to go down in the annals of computer simulation methodolgy as a textbook teaching case of method failure, reliability engineers breathing their own exhaust and considering their own simulator as a valid replacement for the physical thing for safety validation. The unfortunate fact is that both Boeing and the FAA should have a technical process in place for ensuring that emergency checklists and procedures are validated against the real thing and not just the sim. My own feeling is that every list important enough to be memorised should be checked in the air. The fact the FAA did not do this for certification means that it will now be necessary to go over all the Max and possibly even NG checklists with a fine tooth comb to look for other cases where the real world might -so very inconveniently- diverge from a well-behaved simulation.
The farce is now such that one does wonder where incompetence stops and full-bleed corruption has taken over. Even the NYT clearly smells a dead rodent.
Edmund