Is it permissible for a praying person to make supplication in each Sajdah (a prostration) of obligatory prayer?
It is permissible for a praying person, whether praying individually, or in congregation, to make supplication during Sujood (prostration) in obligatory, or voluntary prayers. However, it is disliked for the Imam to do so since he is required to spare the prayer performers any sort of hardship, unless he is leading a certain group who don`t mind him extending the prayer.
Is it permissible for a man to marry up to four wives (polygamy in Islam) for pleasure although he can`t afford that?
It is desirable for the man to have one wife if there was no need for him to have more, if he can't afford marriage forthcoming expenses.
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 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.