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.
A man who was on travel prayed Duhr as four Rakhas upon leaving Tafilah heading to Amman. However, on his way to Amman, he prayed Asir as two Rakhas (Shortened). Is what he did correct from an Islamic perspective?
All perfect praise be to Allah, The Lord of The Worlds. May His blessings and peace be upon our Prophet Mohammad and upon all his family and companions.
What he did is correct; he is liable for nothing before Allah The Almighty, since combining and shortening prayers during travel are two separate concessions. Therefore, it is permissible for a traveler to shorten prayer without combining it with another. And Allah The Almighty Knows Best.
Is it permissible for a woman whose menses exceeded (15) days to pray, fast and do what was prohibited on her to do during the latter period?
If the menses exceeded 15 days then it is deemed menstruation, and in this case she is obliged to pray and fast and to do what was impermissible for her to do during the latter period. In addition, she is obliged to make an ablution for each obligatory prayer after it's due time and making sure that impuity is removed. Finally, your menstruation period is over (Questioner) simlar to your menstruation in the previos month.
Is it permissible to delay menses by using medication in order to fast Ramadhaan?
It is permissible for a woman to use medication in order to delay her menses so that it becomes eligible for fasting Ramadhaan, but it is better that she doesn`t do so, and taking the medication is prohibited if she, or her doctors knew that it involves risk on her health. And Allah Knows Best.