Is it permissible for someone who is unable to fast to pay the fidyah (ransom/compensation payment) to himself, due to his own poverty?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah ﷺ.
It is not permissible, nor does it fulfill the obligation, for a sick person who is currently and permanently unable to fast to pay the fidyah (ransom/compensation payment) to himself, since it is a financial obligation owed by him, established as a standing debt upon him — much like any other debt he owes. If he were to pay it to himself, it would not thereby be discharged. So if he cannot find [anyone eligible to] pay it to, it remains a standing obligation upon him, and is not thereby waived. If Allah, the Mighty and Majestic, later grants him wealth, it becomes obligatory upon him to pay it out to the poor and needy.
Imam al-Khaṭīb ash-Shirbīnī (raḥimahullāh) said: "There is no difference in the obligation of the fidyah between the wealthy and the poor person; its benefit lies in its remaining established as a standing debt upon the poor person [until he is able to pay it] — and this is the more correct position (al-aṣaḥḥ), as indicated by the wording of ar-Rawḍah and its source text." [Mughnī al-Muḥtāj, Vol.2/P.174]
Accordingly: it is not permissible for a Muslim to pay the fidyah to himself while he remains poor. If the sick person is poor, he is not obligated to pay the fidyah immediately, and it remains a standing debt upon him until a time when he has sufficient means and wealth. And Allah, the Exalted, knows best.
What is the ruling on praying in congregation at the mosque?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
Congregational prayer (Salat al-Jama‘ah) is a communal obligation (Fard Kifayah) for resident men regarding the performance of the prescribed (obligatory) prayers. For men, praying in congregation at the mosque is better than praying elsewhere, such as at home. On the authority of Abdullah bin Umar, the Messenger of Allah ﷺ said: 'Prayer in congregation is twenty-seven degrees more excellent than the prayer of a person alone' (Reported by Bukhari & Muslim). Furthermore, on the authority of Abu Hurayrah, the Messenger of Allah ﷺ said: 'Shall I not tell you that by which Allah erases sins and raises ranks?' They said, 'Of course, O Messenger of Allah.' He said: 'Performing wudu thoroughly despite difficulties, taking many steps toward the mosques, and waiting for the next prayer after the prayer; that is your Ribat (steadfastness)' (Narrated by Muslim).
As for a woman, her praying in congregation at home is better for her than in the mosque, according to the saying of our Master the Prophet ﷺ: 'Do not prevent your women from attending the mosques, but their homes are better for them' (Narrated by Abu Dawood). Young boys should be encouraged to attend the mosques and congregational prayers so they may become accustomed to them. And Allah the Exalted knows best.
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 hired a private tutor for my son through an academy that sends teachers [to families] and takes a percentage [of their pay]. At the start of the [new] school year, I arranged directly with that same teacher, without the academy's knowledge. What is the ruling on this?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah ﷺ.
The ruling on this matter depends on knowing the specific terms of the agreement and contract concluded with the academy. If the agreement stipulates that no arrangement may be made with any of the students except through the academy itself, then it is not permissible for you to breach the terms of this contract, based on the words of our master, the Messenger of Allah ﷺ: "Muslims are bound by their conditions." (Related by al-Bukhārī)
However, if the agreement pertains only to teaching a specific subject, and the agreement concludes once that subject is finished, then there is no objection to arranging with the teacher to teach other subjects after the contract period has ended, outside of the academy.
Whatever the case maybe, the teacher must uphold the terms of his contract with the academy. And Allah, the Exalted, knows best.