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.
Who should pay the Zakah (obligatory charity) from the orphan`s money?
His/her guardian, and if the latter fails to do so, then the orphan himself/herself is obliged to pay the Zakah once he/she reaches puberty, and is capable of handling his/her own affairs. And Allah Knows Best.
Is it a condition that one should offer two sacrifices for a male newborn?
It is desirable to offer two sheep for a male newborn, and one for a female newborn. Offering one sheep for the male newborn is also permissible as it observes the Prophet`s Sunnah in this regard.
What is the expiation for breaking fast due to being on a journey, or being sick, or being in a state of menstruation?
No expiation is due on the aforesaid categories, but they are obliged to make up for the missed fast. However, if any of them failed to do so while being able to, and the next Ramadhaan has come, then making up for those days is incumbent on him/her , and paying the ransom as well. And Allah Knows Best.