What is the ruling of Islamic Law on supplicating with other than the transmitted (Ma'thur) supplications in prayer?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah.
It is permissible to supplicate (make du'a) during the prayer for anything from the affairs of religion or worldly life, and the prayer is not invalidated by doing so.
Shaykh al-Islam, the Imam an-Nawawi, may Allah have mercy on him, says: "Our madhhab [i.e., the Shafi'i madhhab] holds that it is permissible for a person to supplicate during it [the prayer] with anything that is permissible to supplicate with outside the prayer, from the affairs of religion or worldly life. He may say: 'O Allah, grant me wholesome sustenance, offspring, a house, and a beautiful young wife' — describing her; or: 'O Allah, free so-and-so from prison,' or 'destroy so-and-so,' and other such things — and none of this invalidates his prayer according to us. And this is also the view of Malik, ath-Thawri, Abu Thawr, and Ishaq." [Al-Majmu', Vol.3/P.454]. And Allah, the Exalted, knows best.
Is a person who forgot to make up missed fasts until the next Ramadan began required to pay expiatory compensation (Fidyah) alongside the makeup fast (Qada')?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah.
Whoever forgets to make up missed fasts of Ramadan (Qada') until the following Ramadan begins incurs no sin, pursuant to the statement of the Messenger of Allah (peace and blessings be upon him): "Indeed, Allah has pardoned for my nation their mistakes, their forgetfulness, and that which they are coerced into doing." [Narrated by Ibn Majah, and Al-Bayhaqi in Al-Sunan Al-Kubra]
Furthermore, such an individual is not obligated to pay a expiatory compensation (Fidyah). It is stated in Bushra Al-Karim (p. 580)—one of the authoritative Shafi'i jurisprudential texts: "As for delaying it [the makeup fasts] due to a valid excuse—such as travel, breastfeeding, forgetfulness, or ignorance of the prohibition of delay (even for one living among scholars)—no Fidyah is required. This is because delaying performance during the actual month is permissible due to these excuses; hence, delaying makeup fasts is even more permissible, even if it continues for years."
And Allah Almighty knows best.
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.
What is the ruling on someone who eats or drinks while uncertain about the arrival of dawn, then later finds out that dawn had not yet broken?
If a person does this, their fast remains valid, as it is confirmed that they ate during the night. Similarly, if someone eats while uncertain and remains unsure whether they ate before or after dawn, their fast is still valid. This is based on the maxim of Sharia Law, which states: "Certainty is not removed by doubt." Certainty, here, is the presence of night, and the doubt concerns the arrival of dawn. Therefore, one relies on certainty and disregards doubt.