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.
Is it permissible for the man to go out wearing shorts?
All Perfect Praise is due to Allah, The Lord of The Worlds
It is permissible so long as his Awrah (private part), which is between his navel and knee, is covered. However, the regular wear traditions and modesty are to be observed. And Allah Knows Best
Is it permissible for a person to give the Zakah (obligatory charity) to his daughter-in-law?
Yes, it is permissible for a person to give the Zakah to his daughter-in-law if she was poor, and none provided for particularly by whom are obliged to provide for her. And Allah Knows Best.
Is it permissible for the children of a deceased father to settle his debt from the Zakah (obligatory charity) money due on them?
It is impermissible to use the Zakah of one`s money for settling the debts of the deceased. However, children should settle the debts of their deceased parents out of filial piety. And Allah Knows Best.