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.
If someone regularly fasts the six days of Shawwal, are they obligated to fast them every year?
A person is not obligated to fast the six days of Shawwal every year, even if they have made it a habit. However, someone who regularly performs a good deed should not abandon it as long as they are able.
Is it permissible for a woman to give the ransom (Fidyah) for breaking her fast to her granddaughter (her son`s daughter)?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
It is permissible for a woman to give the ransom (Fidya) for breaking her fast in Ramadan to her granddaughter (her son’s daughter), provided that the girl is poor and her basic needs are not being met by the maintenance (Nafaqah) of those who are lislamically obligated to provide for her. And Allah the Exalted knows best.
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.