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.
What is the ruling on swearing an oath by the Prophet ﷺ, and does such an oath take effect according to Imām Aḥmad ibn Ḥanbal, requiring expiation upon its breach?
All praise is due to Allah, and peace and blessings be upon our master the Messenger of Allah ﷺ.
Swearing an oath by a created being is disliked (makrūh) in our Shāfiʿī school. Shaykh al-Islām Imām al-Nawawī, may Allah have mercy upon him, states: "Swearing by a created being is disliked — such as swearing by the Prophet, the Kaʿbah, Jibrīl, the Companions, or the Prophet's family. Al-Shāfiʿī, may Allah have mercy upon him, said: 'I fear that swearing by other than Allah the Almighty may constitute an act of disobedience.' The scholars of the school explained this to mean: that is, something forbidden and sinful — indicating that he had some hesitation in the matter. Al-Imām stated: the established position of the school is that it is categorically not forbidden, but rather disliked. Furthermore, whoever swears by a created being, his oath does not take effect and no expiation (kaffārah) is required if he breaks it." [Rawḍat al-Ṭālibīn wa ʿUmdat al-Muftīn, Vol. 11/P.6]
According to the Ḥanbalī school, however, expiation becomes obligatory upon one who swears by our master the Prophet ﷺ and then breaks his oath. Imām al-Bahūtī al-Ḥanbalī, may Allah have mercy upon him, states: "No expiation is required for swearing by other than Allah the Almighty, even if the oath is broken — because expiation was made obligatory for swearing by Allah and His attributes, out of reverence for His names, and nothing else is equal to Him in this regard... except in the case of swearing by our Prophet Muḥammad ﷺ, for expiation becomes obligatory when one swears by him and then breaks the oath. This was explicitly stated in the narration of Abū Ṭālib, because he is one of the two conditions of the two testimonies of faith by which a disbeliever becomes a Muslim. Ibn ʿAqīl held the view that swearing by any of the other prophets, peace and blessings be upon them all, carries the same ruling." [Sharḥ Muntahā al-Irādāt, Vol. 3/P.441]. And Allah the Almighty knows best.
My father has debts and asked me to repay them years ago, and I promised him I would do so upon his death — is it permissible for me to go back on my promise given that I am unable to repay them, especially since he refuses to contribute to repayment on the grounds that the debt has become my responsibility by virtue of my promise?
All praise is due to Allah, and peace and blessings be upon our master the Messenger of Allah ﷺ.
The established principle is that a father's debt is to be repaid from his own wealth, if he possesses sufficient means. As for the promise made by the son to repay it on his father's behalf, fulfilling such a promise is strongly recommended, and breaking it is considerably disliked. Shaykh al-Islām Imām al-Nawawī, may Allah have mercy upon him, states: "Fulfilling a promise is emphatically recommended, and breaking it is severely disliked. The evidences for this from the Qurʾān and the Sunnah are well known." [Rawḍat al-Ṭālibīn,Vol. 2/P.278] Shaykh al-Islām Imām Zakariyyā al-Anṣārī, may Allah have mercy upon him, further states: "The reason fulfilling a promise is not obligatory and breaking it is not forbidden is that a promise is in the nature of a gift, and a gift does not become binding except upon receipt." [Asnā al-Maṭālib fī Sharḥ Rawḍ al-Ṭālib,Vol. 2/P.487]
Given that the son does not possess the financial means to fulfil his promise to his father, breaking this promise falls beyond his capacity — and Allah does not burden a soul beyond what it can bear. Since the father himself possesses sufficient wealth to settle his own debt, repayment must be made from his own funds. Should he pass away before doing so, the debt is to be settled from his estate. And Allah the Almighty knows best.
Is it permissible for a sick person to pray while sitting on a chair?
All perfect praise be to Allah, The Lord of the Worlds It is permissible for a sick person, who is unable to stand up, to offer prayer while sitting on a chair. If he/she was unable to prostrate while on the chair, the he/she should pray while sitting on the ground, but if he/she was neither able to bow (Roku),nor to prostrate, then he can do them while sitting on the chair. And Allah Knows Best.