Is it permissible to offer Istikhara prayer (seeking guidance) after Witr Prayer (A confirmed Sunnah which is offered after Isha prayer and before Fajir prayer with a minimum of 3 Rak`as and a maximum of 11)?
It is permissible to offer Istikhara before and after Witr prayer as it is permissible at any time except that in which prayer is disliked. And Allah Knows Best.
What is the ruling on a person who broke the fast a day in Ramadan due to hardship?
He/she is obliged to make up that day.
How are gaps filled during congregational prayer?
A praying person is allowed to take two steps in order to fill the gap in the row ahead. If the distance was long and requires much movement, then it is impermissible for one to move to fill it because much consecutive movement (three movements) during prayer invalidates it.
What is the ruling on someone who vowed to fast for two consecutive months, but failed to do so?
He is obliged to fulfill his vow by fasting for two consecutive months, but if he fails to do so then, it remains a debt on him until he either fulfills his vow, or dies. In case of his death, his guardian is supposed to fast on his behalf, or donate food from his estate in return for fasting, but if the guardian fails to do so then, it is all in the Hands of Allah.