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.
What should one who made an intention, at night, to make up for a missed fasting day, but broke his fast on the next day?
One who started making up a missed fasting day, then broke his/her fast without a legitimate reason is considered sinful, and is only obliged to make up for the missed fasting days. 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.
What is the ruling on making a false oath?
Making false oath indulges its maker in Hell; therefore, he is obliged to repent, ask Allah for forgiveness and make an expiation; feeding 10 poor or providing clothes for them and in case of incapability of doing any of latters he should fast for 3 consecutive days. And Allah Knows Best.