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 a financially capable woman to pay the Zakat to her sons or one of them?
It is permissible for a mother to give her children from zakat if they are eligible to receive it, even though she is obligated to provide for them. This is based on the saying of the Prophet Muhammad (PBUH) regarding Zainab, the wife of Abdullah Ibn Mas'ud (may Allah be pleased with them): "Your husband and your children are more deserving of your charity" [Al-Bukhari]. And Allah Knows Best.
When is Istikharah (guidance prayer) Du`a offered, before Tasleem (saying asalamu alikum warahmatu allah wa barakatuh to end the prayer), or after it?
It is offered after Tasleem.
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