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 it permissible for a suitor to go out with his fiancé upon the conclusion of the marriage contract?
Upon the conclusion of the marriage contract, the woman becomes lawful for her husband. However, the customary practice should be observed in this regard since rights could be lost in case of divorce, or death.
Is it permissible for one to give the Zakah (obligatory charity) to his indebted brother?
It is permissible for one to give the Zakah to his brother if he was indebted, or poor.
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.