Can someone who begins a voluntary fast break it?
It is preferable for someone who begins an act of worship not to break it.
Allah the Exalted has said {what means}: "and let not your [good] deeds come to nought!" [Muhammad/33].
However, if a person starts a voluntary fast (nafl) and needs to break it, they are going against what is preferable, but there is no sin upon them.
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.
What is the ruling on using a miswak (tooth-stick) during the day in Ramadan?
It is permissible to use a miswak before noon while fasting. However, according to the Shafi'i school, it is disliked (makruh) after noon in order to preserve the natural effect of fasting in the mouth, as the Prophetﷺ said in authentic hadith:
"The breath of a fasting person is more pleasant to Allah than the fragrance of musk."
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.