If someone regularly fasts the six days of Shawwal, are they obligated to fast them every year?

A person is not obligated to fast the six days of Shawwal every year, even if they have made it a habit. However, someone who regularly performs a good deed should not abandon it as long as they are able.

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 the fasting of a woman who has reached menopause if menstrual blood flows?

If a woman reaches the age of menopause (which is usually sixty-two) and her menses have ceased, then she sees blood after that, and its duration is not less than a day and a night (24 hours), it is menstruation (hayd). If it is less than a day and a night, she is considered as having non-menstrual vaginal bleeding (mustahada), so she fasts and prays. However, she must perform ablution for every obligatory prayer after its time enters, pray immediately, and be treated as a person with a continuous condition. There is no specific end limit for a woman's menstruation; it is possible as long as the woman is alive. And Allah the Almighty knows best.

How is Laylat al-Qadr observed?