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.
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.
Is there zakat on social security savings (retirement benefits)?
If the retirement benefits are received, zakat is due on them for one year. Before receiving them, they are not in the person’s possession to be liable for zakat. And Allah Knows Best.
Should the Zakah (obligatory charity) giver tell the poor recipient that this is the Zakah of his money?
No, he shouldn`t. But, the Zakah giver should make an intention in his heart that it is the Zakah of his money when paying it to the poor. And Allah Knows Best.