Is it permissible to repeat the Istikhara (seeking guidance) prayer, and is it a condition that one should sleep after offering it?
All perfect praise be to Allah,The Lord of The Worlds Istikhara is offered once, but it is permissible to repeat it, and sleeping after offering it is not a condition for its validity. And Allah Knows Best.
Is it permissible for the guardian to give Sadaqa (voluntary charity) from the money of the orphans?
It is impermissible for the guardian to donate from the money of the orphans because he is entrusted with the safekeeping of that money, and is prohibited from donating it.
After a month and a half from the end of postpartum bleeding, my wife occasionally finds a small amount of blood, and she is breastfeeding. What is this blood, and should she fast and pray when she experiences it?
This is postpartum bleeding, so she should not fast or pray until she sees the signs of purity, unless it exceeds sixty days, as the maximum duration for postpartum bleeding is sixty days, and the majority of women experience forty days. If it exceeds sixty days, it is considered irregular bleeding (Istihada). It would be advisable to consult a doctor after the sixty days. And Allah Knows Best.
Is it incumbent on the fiancée to obey her fiancé?
When the woman settles in her husband`s house, it is incumbent on him to provide for her and it is incumbent on her to obey him. Before that, and if the marriage contract had been concluded, then she is lawfully his wife and thus she should abide by custom in treating him, but if the marriage contract hadn`t been concluded, then she should treat him as a non-Mahram (Marriageable).