Great post, justanotherflyer. I call it 'setting expectations' and it applies to situations outside aviation as well. Your description:
" Once airborne, the pressure to keep going just that further mile, to look for the gap in the cloud or the lifting in visibility, can then become intense, for fear of disappointing the companions on board. We've all been there."
Is exactly what I meant by that 'land' decision being a difficult one, and the temptation to 'press on pressing on' is very strong.