Is it permissible for a woman who broke fasting due to a delivery to pay a ransom?
She should make up for the missed fasting days once she becomes ritually pure, but it is impermissible for her to pay a ransom while being able to fast.
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 someone to make a supplication to Allah to marry an already married, or an engaged woman?
No, it isn`t, and the person who does so is sinful before Allah, The Almighty.
What is the ruling on going out wearing a long loose skirt with a long shirt that are neither tight nor revealing and without wearing any makeup?
All perfect praise be to Allah the Lord of the Worlds. May Allah`s peace and blessings be upon our Prophet Mohammad and upon all his family and companions.
This is permissible as long as it doesn`t attract the attention and isn`t considered adornment, and this varies according to the environment in which you live. And Allah The Almighty Knows Best.