BisBoy,
It seems to me that you’re asking the age-old question of where is a line between our effort and Emunah.
my answer to that is that each person is on their own level, and each person has his own dividing line. To me a good test to measure Emunah is to look at how much Yirah a person has. if a person claims to have faith that Hashem will help but has no fear, that is inconsistent. After all, it is the same Hand of Hashem that feeds you as that smacks you.
We need to look around and see how Hashem is involved in our lives and make a determination. Joseph was punished for petitioning the wine steward because he should have had faith in Hashem. but how was he supposed to know where his line was? The answer to that is simple. He was already thrown in a pit before. He was miraculously saved from the pit of snakes and scorpions before, so now he should know the Hashem is with him and saving him. It seems to me, based on the example of Joseph, the each of us should know our own level. But, it’s not always clear, just like it was not perfectly clear to Joseph.