What should a person who doubted having missed a pillar of prayer do?
All praise be to Allah, The Lord of The Worlds. The prayer of one who doubts having missed one of its pillars is valid, and nothing is due on him/her since having a doubt after offering the act of worship doesn`t undermine its validity. 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."
Is an elderly or chronically ill person required to pay additional fidyah if they delay it beyond the first year?
An elderly person or someone permanently unable to fast must pay fidyah by feeding one needy person for each missed day.
However, if they delay paying fidyah beyond the first year, no additional fidyah is required.
This differs from someone who delays making up missed Ramadan fasts (qada) without a valid excuse until the next Ramadan begins—such a person is required to pay an additional fidyah for the delay.
Should a prayer performer who forgets to offer the middle Tashahod (saying ash-hadu anala ilaha ila-alah) offer Sujood As-Sahw (prostration of forgetfulness)?
He/she should offer two prostrations of forgetfulness at the end of the prayer. And Allah Knows Best.