What is the ruling of Islamic Law on a person who abandons prayer after reaching puberty—is he required to make them up?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah.
Making up missed obligatory prayers is an Islamic duty just as performing them in their proper time is obligatory, and taking care of them takes precedence over performing voluntary prayers. This is established by the practice of our Supreme Prophet (peace and blessings be upon him) when the polytheists distracted him on the Day of the Trench from performing the Asr prayer, so he made it up afterward, as well as the Hadith: "Pay Allah what is due to Him, for Allah is most deserving of fulfillment." (Recorded by Al-Bukhari)
Furthermore, it is valid to make up missed prayers at any time.
Whoever has missed a number of prayers and does not know their exact count, it is obligatory upon them to sincerely repent and exert their utmost effort to estimate their number. If they are unable to determine the exact count, they should base it on what is most probable according to their best judgment. They should then make them up gradually; if one performs one missed prayer alongside every current obligatory prayer, the matter becomes easy and manageable, and with the passage of time, one will complete what is owed, Allah willing. And Allah Almighty 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.
What is the wisdom behind the legislation of fasting?
Fasting is a divine school from which the believer learns much and trains in virtues that may be needed in life. Among these virtues is patience, as it is the month of patience. Fasting also teaches honesty and consciousness of Allah in both private and public, for there is no observer over the fasting person in abstaining from lawful pleasures except Allah alone.
Fasting strengthens willpower, sharpens determination, and nurtures mercy and compassion among the servants of Allah. It is a struggle against the self, a restraint of desires, a purification of the soul, and a cultivation of goodness.
The Prophetﷺ said: "Allah, the Almighty, said: ‘Every deed of the son of Adam is for him, except for fasting; it is for Me, and I shall reward for it. Fasting is a shield. So when one of you is fasting on a day, let him not engage in obscene speech or raise his voice in anger. If someone insults him or fights him, let him say: I am a fasting person. By Him in whose hand is the soul of Muhammad, the breath of the fasting person is more pleasant to Allah than the fragrance of musk.’" [Bukhari and Muslim]
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.