What type of illness that permits breaking the fast in Ramadan?
It is an illness that, if one fasts, there is a fear it may lead to their death or cause unbearable hardship.
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 the ruling on istibra' and how is it performed?
Istibra' (cleansing from urine) is recommended. It is for a person to ensure that nothing remains of urine in its passage before performing istinja'. Its method is: to clear the throat (or cough slightly), shake the penis (meaning to pass fingers along it to expel any remaining urine if needed), and walk a few steps to the extent that one thinks nothing of urine remains if walking is needed. Each person knows his own nature best. The preferred opinion is that this differs among people. The objective is for one to think that nothing remains in the urinary passage that he fears will exit later. And Allah the Almighty knows best.
What is the Islamic ruling on smearing the head of the newborn with the blood of the `Aqiqah?
All praise is due to Allah, and may peace and blessings be upon our Master, the Messenger of Allah.
It is disliked (makrūh) to smear the head of the newborn with the blood of the 'aqīqah, as this is a practice that belongs to the customs of the pre-Islamic era of ignorance (Jāhiliyyah). What is Sunnah instead is to anoint the newborn's head with saffron or another pleasant fragrance. And Allah Almighty knows best.