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 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.
Is supplicating in Qunoot, at times of affliction, during obligatory and voluntary prayer a Sunnah, and should it be done before Rukoo` (bowing), or after it?
At times of affliction, it is a Sunnah that Muslims supplicate in Qunoot after the final Rukoo` of each obligatory, or voluntary prayer as individuals, or in congregation.
Is Zakah (obligatory charity) due on the Zakah money received by a poor person, and reached a Nissab (minimum amount liable for Zakah), and a whole lunar year had lapsed over having it in his possession?
Yes, the poor who possessed a Nissab for a whole lunar year is obliged to pay the Zakah due on that money even if it was given to him as a Zakah money in the first place. And Allah Knows Best.