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 an elderly person, a pregnant woman, or someone with a chronic illness to pay fidyah before Ramadan begins?
It is not permissible for an elderly person, a pregnant woman, or someone with a chronic illness to pay fidyah before Ramadan begins.
Additionally, it is not allowed to pay fidyah for more than one day in advance, because fidyah is a substitute for fasting, and fasting is not yet obligatory at that time.
However, it is permissible to pay fidyah for a single day in advance, by analogy with paying zakat up to one year in advance.
Is it permissible for one to give the Zakah (obligatory charity) to his indebted brother?
It is permissible for one to give the Zakah to his brother if he was indebted, or poor.
Is it permissible to give to the poor from among the People of the Book from the Udhiyah?
Praise be to Allah, and prayers and peace be upon our Master the Messenger of Allah.
It is permissible to give to the poor among the People of the Book from a voluntary sacrifice (uḍḥiyyat taṭawwuʿ), just as it is permissible to give charity (ṣadaqah) to them. This opinion is a view (wajh) within the Shāfiʿī school, which was favored by al-Muḥibb al-Ṭabarī and Imam al-Nawawī. [See: Ḥāshiyat Ibn Qāsim al-ʿAbbādī ʿalā Tuḥfat al-Muḥtāj (Vol.9/P.365)]. And Allah Almighty knows best.