Is washing both openings (Istinjaa`) a must before every ablution?
Washing the front and back openings (Istinjaa`) is a must in case they have an impurity, but if they do not, there is no need for that, and Istinjaa` is not a condition for the validity of ablution.
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 it incumbent on a father to cover the marriage costs of his son if the latter couldn`t afford them?
The son should seek the help of his relatives in order to convince his father to do the aforesaid, and the father should make sure that his son doesn`t commit fornication through helping him to get married, and Allah will reward him for doing so.
Is Zakah (obligatory charity) due on the items used in the trading process such as: cars , shops etc..?
No Zakah is due on equipments used in the trading process such as cars and the like.