In what matters is istikharah performed? And what is the ruling on repeating it?

Question:
...in a matter that is certain, or in a matter in which there is hesitation?

Answer:
In a matter where there is hesitation: either regarding the path to it, its outcome, its benefit, or something similar, meaning: there is a degree of hesitation in it.
As for something that is known, with no doubt in it, it does not require istikharah. One does not perform istikharah: does he pray the midday prayer or not? He does not perform istikharah. Does he pray the sunset prayer or not? He does not perform istikharah. Does he pray the morning prayer or not? He does not perform istikharah. Does he maintain his family ties or not? Does he be dutiful to his parents or not? These are matters known from the religion, settled.
Q: Does this matter relate to travel, such as Hajj, for example?
A: Hajj is the same. For example, Hajj: there may be fear. If there is fear and danger, he performs istikharah. But if the road is safe and there is no danger there, there is no istikharah.
Q: The repetition?
A: Until his chest is expanded. It is recommended that he also consult after the istikharah. He should consult those he trusts: [Surat al-Shura:38], [Surat Ali 'Imran:159].
Q: Is it permissible to repeat it more than twice?
A: There is nothing wrong with it; until he is reassured and his chest is expanded for one of the two matters.