Can someone who begins a voluntary fast break it?
It is preferable for someone who begins an act of worship not to break it.
Allah the Exalted has said {what means}: "and let not your [good] deeds come to nought!" [Muhammad/33].
However, if a person starts a voluntary fast (nafl) and needs to break it, they are going against what is preferable, but there is no sin upon them.
I read the Qudsī ḥadīth: "Whoever breaks his wuḍūʾ and does not perform ablution has shown me harshness; whoever performs ablution and does not pray has shown me harshness; whoever prays and does not supplicate to Me has shown me harshness; and whoever supplicates to Me and I do not answer him, then I have been harsh to him, and I am not a harsh Lord." What is the authenticity of this ḥadīth?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah.
This ḥadīth was mentioned by al-Ṣaghānī (may Allah have mercy on him) in al-Mawḍūʿāt (p. 43), where he said: “Among them is their saying: ‘Whoever breaks his wuḍūʾ and does not perform ablution has shown me harshness; whoever performs ablution and does not pray has shown me harshness; (whoever prays and does not supplicate to Me has shown me harshness); and whoever supplicates to Me and I do not answer him, then I have been harsh to him, and I am not a harsh Lord.’”
Al-ʿAjlūnī (may Allah have mercy on him) cited what al-Ṣaghānī said in Kashf al-Khafāʾ (Vol.2/p.264). And Allah Almighty knows best.
Can a person required to give kaffarah feed it to their own family members?
The kaffarah must be given to the poor and needy who are not financially dependent on the one giving the kaffarah.
If a person feeds it to their own family members, it does not count as kaffarah, and their obligation remains unfulfilled.
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]