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 a woman sinful if she fasts out of shyness from her family while menstruating or in postnatal bleeding?
It is forbidden for a woman who is menstruating or in postnatal bleeding to abstain from food and drink with the intention of fasting. If she fasts out of shyness, she is sinful, as her fast is not valid.
However, if she refrains from eating and drinking without intending to fast, it is not forbidden, but she unnecessarily burdens herself without need.
What is the ruling on bypassing a nearby mosque for a distant one?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
If a distant mosque has a larger congregation (Jama‘ah) while the congregation in the nearby mosque is smaller, and the congregation in the nearby mosque is not adversely affected by the worshiper's absence, then it is better for him to pray in the distant mosque with the larger congregation. However, if the congregation in the nearby mosque would be affected by his absence—such as if he is its Imam, or if his presence encourages others to attend—then praying in the nearby mosque is better. This ensures that the congregation is established in two different locations within the community. This is based on the saying of the Prophet ﷺ: 'A man's prayer offered with another man is purer than his prayer which he offers alone, and his prayer with two men is purer than his prayer with one and if they are more (in number), it is more beloved to Allah, the Mighty the Majestic' (Narrated by Ahmad, Abu Dawood, and An-Nasa'i). And Allah the Exalted knows best.
What is the ruling on a woman who takes medication to delay menstruation for fasting?
If a woman takes medication (to delay menstrual period) and does not experience menstruation, her fast is valid. However, she is not advised to do so unless there is a necessity.
If the medication harms her, even potentially, it is forbidden (haram) for her to take it.