I understand the reasoning (from an airline and from a manufacturer perspective) for not including a modern EICAS in the 737, but it seems like everyone was so resistant to spending any money that they boxed themselves into a corner where there's now no obvious way to issue a stopgap software fix for the 737 MAX. Without at least automating alerting around the conditions that could lead to failure, we're now depending on pilots' memory and not being engaged in other ongoing things. It's become a problem which could now unintentionally compound other problems. I've heard the argument from Southwest, at least, that the true reasoning behind this is concern about the mental tax of having to switch between two different cockpit configurations and the potential for pilot error in those cases. It rings a little hollow in the context of Southwest trying to avoid "expensive simulator training" at the same time, however.
I am not going to profess to be enough of an expert in the economics of airliner design to say that there was a better option than continuing to re-engine the 737, but it really, really feels like Boeing is overdue for a clean sheet replacement for the 737 and have pushed things way too far.