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 incumbent on a family to provide for its old handicapped son and take care of him?
The family and relatives - e.g. brothers - of such a person are obliged to spend on him and take care of him if he didn`t have money of his own.
Is supplicating in Qunoot, at times of affliction, during obligatory and voluntary prayer a Sunnah, and should it be done before Rukoo` (bowing), or after it?
At times of affliction, it is a Sunnah that Muslims supplicate in Qunoot after the final Rukoo` of each obligatory, or voluntary prayer as individuals, or in congregation.
Is it permissible to offer Istikhara prayer (seeking guidance) after Witr Prayer (A confirmed Sunnah which is offered after Isha prayer and before Fajir prayer with a minimum of 3 Rak`as and a maximum of 11)?
It is permissible to offer Istikhara before and after Witr prayer as it is permissible at any time except that in which prayer is disliked. And Allah Knows Best.