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 Zakah (obligatory charity) obligatory on indebted merchant?
Debt doesn`t abrogate the dueness of Zakah, thus a debtor who has money, articles of merchandise, or other Zakah funds at his disposal should pay their Zakah.
Is it permissible to make up missed prayers at the times in which praying is disliked?
All perfect praise be to Allah,The Lord of The Worlds It is permissible to make up missed prayers at any time even that in which praying is disliked. Absolute supererogatory prayer is forbidden to be performed at the times in which praying is disliked, and this also applies to Ihram and Istikhara prayers. However, there is no harm in offering prayers in Mekah during those times. And Allah Knows Best.
After a month and a half from the end of postpartum bleeding, my wife occasionally finds a small amount of blood, and she is breastfeeding. What is this blood, and should she fast and pray when she experiences it?
This is postpartum bleeding, so she should not fast or pray until she sees the signs of purity, unless it exceeds sixty days, as the maximum duration for postpartum bleeding is sixty days, and the majority of women experience forty days. If it exceeds sixty days, it is considered irregular bleeding (Istihada). It would be advisable to consult a doctor after the sixty days. And Allah Knows Best.