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 bleeding that lasts for nine or ten days considered menstruation (Hayd)?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
If the duration of the bleeding does not exceed fifteen days, then all of it is considered menstruation (Hayd), even if the regular cycle ('Adah) has changed. And Allah the Exalted knows best.
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 performing the Istikhara prayer after the Witr paryer?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
The Istikhara prayer (Prayer for seeking guidance) is a Sunnah. It consists of two units (rak’ahs) performed outside of the obligatory prayers, after which the person supplicates with the traditionally narrated du’a. It is permissible to perform it before or after the Witr prayer, as the Istikhara prayer is recommended at all times except during the disliked times—the periods in which prayer is prohibited. This is because its specific reason (the Istikhara and supplication) occurs after the prayer itself, and any prayer with a subsequent reason is not permitted during the prohibited times. It should be noted that the two rak’ahs of Istikhara are not fulfilled by performing only one rak’ah, nor by a prostration of recitation (Sajdat al-Tilawah), nor by a funeral prayer (Janazah). And Allah the Exalted knows best.