Is it permissible for a person who has to make up for missed fasts to fast six days of Shawwal (the month directly after Ramadan) before making up for the missed fasts?
Yes, it is permissible for him/her to do so, but it is better that they make up for missed fasts first. And Allah Knows Best.
I took a car from the Orphans' Fund Development Institution; is there usury (Riba) involved in this transaction?
If the Sharia's conditions were met, then there is no harm in this. And Allah The Exalted Knows Best.
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.
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.