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.
What is required of one who doubts the number of rakʿāt during prayer?
All praise is due to Allah, and peace and blessings be upon our master the Messenger of Allah ﷺ.
If a person doubts the number of rakʿāt he has prayed, he should build upon the lesser number, as that is what he is certain of. He should then perform the prostration of forgetfulness (sujūd al-sahw) before the final salām at the end of the prayer. ʿAṭāʾ ibn Yasār narrated that the Messenger of Allah ﷺ said: "When any one of you is in doubt during his prayer and does not know whether he has prayed three rakʿāt or four, let him pray one more rakʿah and then perform two prostrations while seated before the salām. If the rakʿah he prayed was a fifth, these two prostrations will make it even; and if it was the fourth, then the two prostrations serve as a humiliation for the devil." (Reported by Abū Dāwūd.)
It is stated in al-Muqaddimah al-Ḥaḍramiyyah — one of the foundational texts of the Shāfiʿī school: "If one doubts whether he has prayed three rakʿāt or four, he is obliged to build upon the lesser number."
However, if such doubt recurs repeatedly and reaches the level of obsessive whispering (waswasah), he should not build upon the lesser number in that case — rather, he should build upon the greater number. And Allah the Almighty knows best.
What is the ruling on someone who intends to travel to Jeddah for two days — must he enter iḥrām from his place of residence [i.e., before passing the mīqāt]?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah ﷺ.
Whoever is firmly resolved in his intention to perform ‘Umrah before setting out on his journey, it is unlawful for him to pass beyond his country's mīqāt (the designated boundary point for entering the state of iḥrām) without entering iḥrām. If he does so, he must return to the mīqāt to enter iḥrām from there, provided he has not yet begun performing the rites of the pilgrimage — in which case nothing further is required of him. However, if he does not return, he must offer a sacrifice (sheep/goat), to be distributed among the poor of the Ḥaram.
It is stated in at-Tanbīh fī al-Fiqh ash-Shāfi‘ī (p. 71): "Whoever, intending to perform the rites [of ‘Umrah or Ḥajj], passes beyond the mīqāt and enters iḥrām only after it, must offer a sacrifice. However, if he returns to the mīqāt before beginning any of the rites, the sacrifice is waived from him."
Accordingly: whoever is firmly resolved in his intention to perform ‘Umrah before setting out on his journey must enter iḥrām at the mīqāt of his country through which he passes. Whoever fails to do so, passing beyond the mīqāt without entering iḥrām, and does not return, has sinned, and must repent to Allah, the Exalted; and he must offer a sacrifice, to be distributed among the poor of the Ḥaram. And Allah, the Exalted, knows best.
Is it permissible to give multiple mudds (portions) of fidyah to a single person?
Yes, it is permissible to give multiple mudd of fidyah to a single person, because each day of fasting is considered an independent act of worship.