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 praying person to make supplication in each Sajdah (a prostration) of obligatory prayer?
It is permissible for a praying person, whether praying individually, or in congregation, to make supplication during Sujood (prostration) in obligatory, or voluntary prayers. However, it is disliked for the Imam to do so since he is required to spare the prayer performers any sort of hardship, unless he is leading a certain group who don`t mind him extending the prayer.
Who should pay the Zakah (obligatory charity) from the orphan`s money?
His/her guardian, and if the latter fails to do so, then the orphan himself/herself is obliged to pay the Zakah once he/she reaches puberty, and is capable of handling his/her own affairs. And Allah Knows Best.
What is the ruling on performing Tahajjud after the Witr?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
It is permissible for one who has prayed the Witr to perform voluntary (Nafl) prayers after it. However, it is preferable for the Witr to be the final prayer of the night. Therefore, if a person is confident that they will wake up during the night for Tahajjud, it is recommended for them to delay the Witr until after the Tahajjud. Conversely, if one fears they may not wake up, they should perform the Witr before sleeping.
Al-Khatib al-Shirbini (may Allah have mercy on him) stated: 'It is not disliked (Makruh) to perform Tahajjud after the Witr, but it is not recommended to do so intentionally.' [Mughni al-Muhtaj, Vol. 1/P.454]. And Allah the Exalted knows best."