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 working for orphans' institution?
Praise be to Allah the Lord of the Worlds. May His peace and blessings be upon our Prophet Mohammad and upon all his family and companions.
There is no sin in working for orphans` institution. And Allah The Almighty Knows Best.
Is it permissible to offer Tahajjud prayer after Witr prayer?
It is permissible to offer voluntary prayer after Witr (An odd number prayer performed between Isha and Fajr) prayer. However, it is desirable that the night prayer be ended with Witr. Therefore, it is desirable for one, who thought that he was most probably going to wake up at night in order to offer Tahajjud, to offer Witr after it, but one, who fears that he might not wake up, should offer Witr before going to bed.
A man break his fast once during Ramadan and he already have an expiation of fasting for two consecutive months. He fasted for a month and passed away. Is it permissible for his sons to fast the remaining month equally?
Fasting for expiation must be performed consecutively. I advise his children to feed sixty poor people, giving each one half a kilogram of rice or its monetary equivalent. This is because if a living person is unable to fast, they are required to feed sixty poor people, and death constitutes an inability. And Allah The Almighty Knows Best.