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 woman shaking hands with the brothers of her husband`s father, and not putting on Islamic wear before them?

The aforesaid are strangers to the their brother`s son`s wife, therefore, it is forbidden for her to take off her Islamic wear before them, or to shake hands with them.

When Iddah is Initiated for Deceased's Wife?

All perfect praise be to Allah, The Lord of The Worlds, and may His Peace and Blessings be upon our Prophet Muhammad and upon all of his family and companions.

Iddah is observed on the same date at which her husband passed away for four months, but as for the pregnant, it is observed at the date she gives birth. And Allah Knows Best. 

Is it permissible for the mother to offer an Aqeeqah (the sheep slaughtered on the seventh day from the child`s birth)for her son?

Aqeeqah is due on the one obliged to provide for the newborn, and it is permissible for the grandfather, or the mother to offer the Aqeeqah.