Is it permissible for a person who has to make up for missed fasts to fast six days of Shawwal (the month directly after Ramadan) before making up for the missed fasts?
Yes, it is permissible for him/her to do so, but it is better that they make up for missed fasts first. 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 woman to adorn herself with kohl (eyeliner) and go out wearing it?
Kohl is a form of adornment, and it is forbidden for a woman to display her adornment to anyone other than her husband or a Mahram. And Allah Knows Best.
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.