Should a person feel pleased, or have a virtuous vision after offering Istikhara (guidance prayer) in order to do what he/she had offered it for?
The result of the Istikhaarah is not necessarily that a person sees something (in his dream), or feels pleased, but the most important result of the Istikhaarah is whether a person is enabled to do a given matter or not.
Is it permissible for a woman to wear underwear while performing Umrah?
Yes, it is permissible for a woman to wear underwear while performing Umrah. This is because she should keep her regular clothes that cover all her body while being in a state of Ihram (ritual consecration) for Hajj, or Umrah. However, she should uncover her face and hands, but it is permissible for her to let her head-covering garment drape from her head down over her face when non-Mahram (i.e., marriageable) men pass by her. And Allah Knows Best.
What is the ruling on a man leading his sisters in obligatory prayer, or Taraweeh prayer (Night prayer in Ramadan)?
The prayer of the man who leads his wife, or sisters in prayer is valid, but it is more rewarding for him to offer obligatory prayer in the mosque. And Allah Knows Best.
Is it incumbent on the fiancée to obey her fiancé?
When the woman settles in her husband`s house, it is incumbent on him to provide for her and it is incumbent on her to obey him. Before that, and if the marriage contract had been concluded, then she is lawfully his wife and thus she should abide by custom in treating him, but if the marriage contract hadn`t been concluded, then she should treat him as a non-Mahram (Marriageable).