Yes, that tradeoff always exists. There are always edge cases. The pilot will always need specific 'additional' information about the plane to avoid crashing.

The choice to make is how difficult you will allow features to be, and how many difficult features you will add.

The answer has to be at least moderately high to get the plane off the ground. If it's too high then you have a bunch of deaths.

It's okay to say Boeing went too far on the scale, but to say they never should have been on the scale is misguided. Intelligence of the operator has to cover for certain aspects of the design.