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.
Am I Permitted to Use Ill-gotten Money given to me from Sorcerer's Sons during during my Mother's condolence?
You are permitted to use this money if you were ascertain that the majority of his lawful money surpasses the unlawful one. 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 a person who isn`t able to fast due to old age, or an incurable disease?
Paying the ransom is due on such a person, and that is giving a Mud (600 grams) of wheat, or rice, or the price of that amount to a needy Muslim for each missed fasting day. And Allah Knows Best.