Can I start fasting based on the moon sighting of another country?
You must follow the moon sighting of the country you are in.
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 should a person do if they suffer from an incurable illness that prevents them from fasting?
A person who has an illness that is not expected to be cured and prevents them from fasting must feed a needy person one mudd (600 grams) of food (such as wheat or rice) for each missed day instead of fasting.
Allah Almighty says {what means}: "and [in such cases] it is incumbent upon those who can afford it to make sacrifice by feeding a needy person." [Al-Baqarah/184].
Is the prayer of a woman who is led by an Imam via T.V. permissible?
All perfect praise be to Allah, The Lord of The Worlds, and may His Peace and Blessings be upon our Prophet Muhammad and upon all of his family and companions. Amongst the conditions for the validity of prayer is that both the Imam and those led by him must be in the same place. Thus, the prayer of the person who is being led by a televised Imam is invalid unless he/she was with him in the same mosque. And Allah Knows Best.