Is it permissible for someone to make a supplication to Allah to marry an already married, or an engaged woman?

No, it isn`t, and the person who does so is sinful before Allah, The Almighty.

When Iddah is Initiated for Deceased's Wife?

All perfect praise be to Allah, The Lord of The Worlds, and may His Peace and Blessings be upon our Prophet Muhammad and upon all of his family and companions.

Iddah is observed on the same date at which her husband passed away for four months, but as for the pregnant, it is observed at the date she gives birth. And Allah Knows Best. 

Is it incumbent on a father to cover the marriage costs of his son if the latter couldn`t afford them?

The son should seek the help of his relatives in order to convince his father to do the aforesaid, and the father should make sure that his son doesn`t commit fornication through helping him to get married, and Allah will reward him for doing so.

If a woman makes a vow to slaughter a sheep, and her husband is the one who buys it for her from his own money, and he says: "It is for you until you fulfill your vow with it," Is this permissible, or must she buy it herself from her own money?

If her husband gave her the sheep as a donation for the puprose of fulfilling the oath she made and was slaughtered by the wife or the husband on her behalf then the vow she made is fulfilled. And Allah Knows Best.