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.
Is it permissible to offer Istikhara prayer (seeking guidance) after Witr Prayer (A confirmed Sunnah which is offered after Isha prayer and before Fajir prayer with a minimum of 3 Rak`as and a maximum of 11)?
It is permissible to offer Istikhara before and after Witr prayer as it is permissible at any time except that in which prayer is disliked. And Allah Knows Best.
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.
Are dream interpretation books accurate?
All perfect praise be to Allah the Lord of the Worlds. May His peace and blessings be upon Prophet Mohammad and upon all his family and companions.
Dream interpretation books are unreliable because they are merely expectations, not rulings of Sharia. However, if one sees a dream which one does not like, one should spit on one's left side and seek the refuge of Allah from the satan; it will not do one any harm, and one should not disclose it to anyone. If one sees a good vision, one should feel pleased but should not disclose it to anyone but whom one loves. And Allah The Almighty Knows Best.