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 make up for the missed fasts of the deceased?
A deceased`s missed fasts should be made up for by his/her guardian. It is also permissible to make up for the missed fasts of a deceased relative, and to pay a ransom in expiation for the latter`s missed fasts, which is feeding a needy person for every missed day. However, the guardian`s permission need to be sought by the non-relatives of the dead to fast on his behalf. 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.
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.