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.
I read the Qudsī ḥadīth: "Whoever breaks his wuḍūʾ and does not perform ablution has shown me harshness; whoever performs ablution and does not pray has shown me harshness; whoever prays and does not supplicate to Me has shown me harshness; and whoever supplicates to Me and I do not answer him, then I have been harsh to him, and I am not a harsh Lord." What is the authenticity of this ḥadīth?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah.
This ḥadīth was mentioned by al-Ṣaghānī (may Allah have mercy on him) in al-Mawḍūʿāt (p. 43), where he said: “Among them is their saying: ‘Whoever breaks his wuḍūʾ and does not perform ablution has shown me harshness; whoever performs ablution and does not pray has shown me harshness; (whoever prays and does not supplicate to Me has shown me harshness); and whoever supplicates to Me and I do not answer him, then I have been harsh to him, and I am not a harsh Lord.’”
Al-ʿAjlūnī (may Allah have mercy on him) cited what al-Ṣaghānī said in Kashf al-Khafāʾ (Vol.2/p.264). And Allah Almighty knows best.
What is the ruling on making up missed fasts from many years?
A Muslim must make up for any missed fasts, as they are a debt owed to Allah. The Prophet ﷺ said:
"The debt owed to Allah is more deserving of being fulfilled." [Narrated by Muslim]
Whoever has missed fasts must make them up as long as they are alive and capable of fasting.
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.