Is it permissible for a person who has to make up for missed fasts to fast six days of Shawwal (the month directly after Ramadan) before making up for the missed fasts?
Yes, it is permissible for him/her to do so, but it is better that they make up for missed fasts first. And Allah Knows Best.
Is it permissible to openly announce the engagement of a woman who is in her waiting period (iddah)?
It is not permissible to openly announce the engagement of a woman in her waiting period (Iddah), but it is permissible to hint (imply) at it if she is in her waiting period after the death of her husband. And Allah Knows Best.
What is the ruling on a man leading his sisters in obligatory prayer, or Taraweeh prayer (Night prayer in Ramadan)?
The prayer of the man who leads his wife, or sisters in prayer is valid, but it is more rewarding for him to offer obligatory prayer in the mosque. And Allah Knows Best.
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.