What should a person, who doubts the validity of his Wudu, or over performs it, do?

One who doubts the validity of his/her Wudu while performing it should redo it until he/she is certain of having attained purity. But, if doubt was after having performed Wudu, then he/she should not pay attention to that as doubt after the end of an act of worship does not count. This is of course in case doubt was within the reasonable limits since once it goes beyond that, it becomes a whispering of the Shaytaan (devil) which he/she should ignore as the Wudu is valid.

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 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.

Generally speaking, I`m dutiful to my mother and opt for obeying her. However, she chose a certain girl to be my future wife, but I`m not pleased with her choice although that girl comes from a good family and enjoys good character. Should I obey my mother or choose another girl that lives up to my expectations?

Praise be to Allah the Lord of the Worlds.

One must obey their parents in whatever is in compliance with the teachings of Sharia and within one`s capacity. However, you aren`t to blame for not marrying that girl, but it is better that you tell your mother about that and it is preferable that you perform Istikharah prayer. And Allah The Almighty Knows Best.