Is it permissible to repeat the Istikhara (seeking guidance) prayer, and is it a condition that one should sleep after offering it?
All perfect praise be to Allah,The Lord of The Worlds Istikhara is offered once, but it is permissible to repeat it, and sleeping after offering it is not a condition for its validity. And Allah Knows Best.
Is permissible to buy/sell with non-Muslim?
Yes buying/selling for a Muslim with non-Muslim is permissible as regards what is lawful.
I took a housing loan from the bank for a 20-year period. Four years have passed, and I recently learned that this loan is usurious. I wish to perform Umrah. Am I permitted to perform it? If not, what should I do?
You are permitted to perform Umrah. Strive to repay the debt in hopes of reducing the amount of usurious interest. Allah Says (What means): "And there are others who have acknowledged their sins. They had mixed a righteous deed with another that was bad. Perhaps Allah will turn to them in forgiveness. Indeed, Allah is Forgiving and Merciful." [At-Tawbah/102]. 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.