Is it permissible for a man to wear transparent clothing?
It is not permissible for a man to wear transparent clothing that reveals his 'Awrah (the area that must be covered). The 'Awrah of a man is "from his navel to his knees", and modesty is more prudent. And Allah Knows Best.
Is it permissible to offer mandatory prayer while sitting?
All perfect praise be to Allah, The Lord of The Worlds, and may His Peace and Blessings be upon our Prophet Muhammad and upon all of his family and companions. Standing up is a pillar in the mandatory prayer and the prayer is not valid without it unless one cannot do it. As for Nafila (supererogatory prayer), one can perform it in the state of sitting even if he/she can stand, but his/her reward is half the reward of the person who prays while standing if he/sh has no legal excuse for such an act. And Allah Knows Best.
Is it permissible for a man to marry up to four wives (polygamy in Islam) for pleasure although he can`t afford that?
It is desirable for the man to have one wife if there was no need for him to have more, if he can't afford marriage forthcoming expenses.
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.