The FAA has not been an unchanaging entity operating under an unchanging set of rules for the past 30 years.
In reality, major changes have been made to the way that the FAA operates and delegates authority in a series of sweeping changes since 2005 that were largely meant to cover for the fact that Congress has been severely underfunding the FAA.
The MAX is one of the first models we’ve seen wholly designed and manufactured under this new process. (substantial amounts of the underlying safety analysis of the 787 happened under the old setup)
One major change that may be relevant in this case is that whereas Designated Engineering Representatives used to do safety analysis work at Airplane manufactures in a completely parallel, firewalled cross-cutting engineering group that effectively reported directly to the FAA in a quasi on-loan model, “in order to reduce costs” the FAA allowed this to be scrapped and replaced with “Airworthiness Representatives” embedded in, and crucially answering to, the regular engineering management at the company. Company management then acts as middle-man to the FAA. AR Management at say Boeing is nominally supposed to act as independent of Boeing and represent FAA opinions, but in practice routinely pushes back on FAA requests and acts to represent the interests of Boeing management: https://www.seattletimes.com/business/delegating-aircraft-sa...
So previously if day-to-day engineering was under pressure from a manager to ship a software subsystem or complete a component design, these deadlines were unrelated to the DERs, who operated in their own safety-focused management chain under the FAA.
Now, the AR is under the same manager and pressures as everyone else to hit the ship date. It is unsurprising that quality of analysis might take a back seat to job security in such a setup.
It does not make much sense to defend the FAA by pointing at successes produced by processes that were no longer in place by the time the 737 MAX engineering programme began.