A: The original plan was to start from the tree line at the bottom of the mountain but the explorers couldn’t set up camp there because of the rain so they moved higher up.
B: The Robertson team should have known that they couldn’t have started from the tree line in the rainy season.
A: Yes, they really should have checked that!
What is the difference if I rewrite it as
The Robertson team should have known that they couldn’t start from the tree line in the rainy season.
The prior phrase "should have known" further reduces my ability to think. I don't know if its existence makes a difference.