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 prayer mandatory on a dying person who goes through a state of unconsciousness, then wakes up?
If he wakes up and was conscious, then he should pray the way/manner he could, but if he wasn't, then he is exempted from obligatory prayer as Allah Says in this regard (What means): "On no soul doth God Place a burden greater than it can bear." [Al-Baqarah/286].
Is the one who gives up on marriage because he can`t afford it considered sinful?
Marriage is desirable, but one who can`t afford it isn`t considered sinful. However, he should supplicate to Allah, and seek His forgiveness.
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.