What is the Islamic ruling on one who was unable to fast and then regained the ability?
He is not required to make up the fast (Qada) even if he becomes capable of it; whether he regained the ability to fast after paying the fidya (feeding a needy person for each day of missed fasting) or before it, because he was liable for paying it in the first place, so it remains binding upon him. However, if he delayed paying it beyond the first year, nothing is required of him due to the delay. If he is unable to pay it, it does not remain as a debt upon him. And Allah the Exalted knows best.
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]
Can I start fasting based on the moon sighting of another country?
You must follow the moon sighting of the country you are in.
What is the ruling on making up missed fasts from many years?
A Muslim must make up for any missed fasts, as they are a debt owed to Allah. The Prophet ﷺ said:
"The debt owed to Allah is more deserving of being fulfilled." [Narrated by Muslim]
Whoever has missed fasts must make them up as long as they are alive and capable of fasting.