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 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.
What is the ruling on praying behind an undesirable Imam?
It is permissible to pray behind an Imam who is undesirable for committing religious violations, and it is disliked for such an Imam to lead the prayer. Still, If he was undesirable for a personal, or a worldly matter, then such argument doesn’t hold water. 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.