Is it permissible for someone to make a supplication to Allah to marry an already married, or an engaged woman?
No, it isn`t, and the person who does so is sinful before Allah, The Almighty.
Is it obligatory for a wife who has been abandoned for many years to observe the waiting period (iddah) after her husband passes away?
If her husband passes away, the wife is required to observe the waiting period (Iddah), even if he had abandoned her, because she is his wife and inherits from him, so she must observe the iddah after his death. 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 I had prayed, I found a drop of menstrual blood and was unsure when that happened; what is the ruling on my prayer and fast?
All praise is due to Allah, peace and blessing be upon the Messenger of Allah.
Your prayer and fast are correct ,and you should not make up for them, and we ask Allah, The Almighty, to duely reward you for these acts of worship. Your menses start once you see blood because the situation remains as such unless there is certainty or predominant conjecture, as per the Fiqh maxim: "Certainty is not removed by doubt". And Allah Knows Best.
