Is Zakah due on the orphan`s money?
Yes, Zakah is due on the money of the orphan.
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.
If the imam does not leave time for reciting Surah Al-Fatihah, is the recitation of Al-Fatihah waived for the follower?
The recitation of Al-Fatihah is not waived for the follower. They should recite it silently, even if it causes a slight delay in following the imam in bowing (Ruku'). And Allah Knows Best.
What is teh ruling on thoughtless oath?
One who swears by Allah unintentionally and isn`t determined to fulfill his oath, nothing is due on him. Allah, The Almighty, Says (What means): "God will not call you to account for thoughtlessness in your oaths, but for the intention in your hearts; and He is Oft-forgiving, Most Forbearing." [Al-Baqarah/225]. However, it is dispraised for a Muslim to swear frequently.