What is the ruling on performing voluntary prayers during official working hours?
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
There is no harm if there was break time during official working hours, but if not then it is impermissible. 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.
Is it permissible for a mother to stop her daughter from marrying a respectable, God-fearing young man because he isn't college/university graduate?
It is impermissible to deny a woman her right in getting married except for a lawful reason, and problems can be solved through dialogue. However, she can file a suit in order for the judge to have a say in that regard.
I`m a mother of three orphans. Is it permissible for me to spend on myself from their salary, such as buying a Jilbab*?
All perfect 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.
It is permissible to take a reasonable amount that is equal to your services to them. However, it is better that you don`t. The evidence on this is that Almighty Allah Says (What means): "Make trial of orphans until they reach the age of marriage; if then ye find sound judgment in them, release their property to them; but consume it not wastefully, nor in haste against their growing up. If the guardian is well-off, Let him claim no remuneration, but if he is poor, let him have for himself what is just and reasonable. When ye release their property to them, take witnesses in their presence: But all-sufficient is God in taking account." [An-Nisa`/6]. And Allah The Almighty Knows Best.
* A full-length outer garment, traditionally covering the head and hands, worn in public by some Muslim women.