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.
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.
Is it permissible for a praying person to make supplication in each Sajdah (a prostration) of obligatory prayer?
It is permissible for a praying person, whether praying individually, or in congregation, to make supplication during Sujood (prostration) in obligatory, or voluntary prayers. However, it is disliked for the Imam to do so since he is required to spare the prayer performers any sort of hardship, unless he is leading a certain group who don`t mind him extending the prayer.
What is the ruling on someone who intends to travel to Jeddah for two days — must he enter iḥrām from his place of residence [i.e., before passing the mīqāt]?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah ﷺ.
Whoever is firmly resolved in his intention to perform ‘Umrah before setting out on his journey, it is unlawful for him to pass beyond his country's mīqāt (the designated boundary point for entering the state of iḥrām) without entering iḥrām. If he does so, he must return to the mīqāt to enter iḥrām from there, provided he has not yet begun performing the rites of the pilgrimage — in which case nothing further is required of him. However, if he does not return, he must offer a sacrifice (sheep/goat), to be distributed among the poor of the Ḥaram.
It is stated in at-Tanbīh fī al-Fiqh ash-Shāfi‘ī (p. 71): "Whoever, intending to perform the rites [of ‘Umrah or Ḥajj], passes beyond the mīqāt and enters iḥrām only after it, must offer a sacrifice. However, if he returns to the mīqāt before beginning any of the rites, the sacrifice is waived from him."
Accordingly: whoever is firmly resolved in his intention to perform ‘Umrah before setting out on his journey must enter iḥrām at the mīqāt of his country through which he passes. Whoever fails to do so, passing beyond the mīqāt without entering iḥrām, and does not return, has sinned, and must repent to Allah, the Exalted; and he must offer a sacrifice, to be distributed among the poor of the Ḥaram. And Allah, the Exalted, knows best.