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 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.
Should a person feel pleased, or have a virtuous vision after offering Istikhara (guidance prayer) in order to do what he/she had offered it for?
The result of the Istikhaarah is not necessarily that a person sees something (in his dream), or feels pleased, but the most important result of the Istikhaarah is whether a person is enabled to do a given matter or not.
Is Iddah (waiting period) incumbent on an old woman whose husband had died?
Upon the death of the husband, Iddah is incumbent on the wife regardless of their age. And Allah Knows Best.