The elephant in the room in this conversation is the fact that in general, people whose Hishtadlus lies in certain fields generally make more money.
A doctor, for example, doesn’t necessarily work harder or more hours than a trucker, but the average income for doctors is significantly higher than it is for truckers.
The question, then, is this:
How do we reconcile this reality with the well known positions of the Torah referred to above?
This is a very complex issue, and much time, thought and research must be devoted to it in order to have, if not a comprehensive explanation, at least a coherent approach.
Two points that I think are very important to contemplate are:
1. Not all people are equally governed by Hashgacha Pratis. To some degree, all people are governed by Teva. [That is to say, the Ratzon Hashem is that the general system He created, to which we refer as Teva, should govern those who do not merit or who, by dint of their own shortcomings, would not benefit from His direct governance.] This naturally results in generalities such as doctors earning more money.
2. Depending on the specific nature of a person’s mission in this world, the way he exercises his Bechira could entail Hashem granting him more money. For example, person whose purpose in life is to be Marbitz Torah, but who chooses to become a lawyer, may be very successful so that he is able to fulfill his purpose by supporting institutions which are Marbitz Torah (Rav Dessler’s example, not mine).