Is it obligatory for a wife who has been abandoned for many years to observe the waiting period (iddah) after her husband passes away?
If her husband passes away, the wife is required to observe the waiting period (Iddah), even if he had abandoned her, because she is his wife and inherits from him, so she must observe the iddah after his death. And Allah 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.
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
What is the ruling on a woman driving a car?
All Perfect Praise is to Allah, The Lord of The Worlds, and may His Peace and Blessinsg be upn our Prophet Muhammad and upon all of his family and compnions.
It is permissible for the woman to drive a car, but it is impermissible for her to travel unaccompanied by a Mahram (Unmarriageable kin). And Allah The Exalted Knows Best.