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.
Am I Permitted to Use Ill-gotten Money given to me from Sorcerer's Sons during during my Mother's condolence?
You are permitted to use this money if you were ascertain that the majority of his lawful money surpasses the unlawful one. And Allah Knows Best.
Is it permissible for a woman to leave her house wearing brightly colored clothing?
Brightly colored clothing is of woman's adornments, however; and this shouldn't be revealed save to her husband and Mahrams. And Allah Knows Best.
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.