Is it permissible to offer Istikhara prayer (seeking guidance) after Witr Prayer (A confirmed Sunnah which is offered after Isha prayer and before Fajir prayer with a minimum of 3 Rak`as and a maximum of 11)?
It is permissible to offer Istikhara before and after Witr prayer as it is permissible at any time except that in which prayer is disliked. 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.
Is it permissible for a person who had vowed to give a certain amount of money to another, but didn`t find the latter to donate that money to the mosque?
In principle, the vowing person should abide by his vow as much as possible. Therefore, if he couldn`t find the person that he had made the vow for, then the vow itself is countless and nothing is due on its maker. However, if the latter happens to find the former later on then, he has to give him that money.
Someone asked me to pay off his debt on his behalf as a loan, without any compensation. When I went to the creditor, he told me that if I paid the full amount at once, rather than in installments, he would give me a certain discount. Is this permissible? And if he applies the discount, to whom does the deducted amount belong?
If part of the debt is paid and the creditor forgives the remaining amount, the waiver is valid, and the remaining debt is no longer the responsibility of the original debtor. The person who paid the debt on behalf of another has no right to claim any portion of the original debt. And Allah Knows Best.