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 woman in her waiting period (Iddah) after her husband's death to leave her house and mix with non-Mahrams?
It is not permissible for a woman in her waiting period (Iddah) after the death of her husband to leave her house except for a necessity, such as for medical treatment, nor is she allowed to mix with non-Mahrams. A woman is not permitted to mix with anyone other than her husband or Mahrams, whether she is in her waiting period or not. However, there is no harm in accepting condolences from those who visit and responding to their inquiries about her well-being. And Allah Knows Best.
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 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.