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.
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.
Is it permissible to pay the Zakah to my grandmother who lives alone in a rented accommodation with bad conditions noting she had three sons.
Zakah cannot be given to ascendants (parents and grandparents). It is obligatory for her sons and grandsons to provide for her, and they would be sinful if they fail to do so. And Allah Knows Best.
Is it permissible to single out Fridays, Saturdays, and Sundays to make up for missed fasting without fasting a day before ,or after each ?
Yes, it is permissible to make up for missed fasting during the aforesaid days, and it is also valid to offer non-obligatory and vowed fasting as well. However, fasting a day before or after each isn`t obligatory. And Allah Knows Best.