Someone wiped over his shoes after wearing them in a state of purity, then took them off and prayed without them?
Ablution is not invalidated by taking off leather socks or shoes after wiping over them. However, whoever takes them off after wiping must wash his feet only. If he prayed without washing his feet, he must wash his feet and repeat the prayer. And Allah the Almighty knows best.
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 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 should a person who doubted having missed a pillar of prayer do?
All praise be to Allah, The Lord of The Worlds. The prayer of one who doubts having missed one of its pillars is valid, and nothing is due on him/her since having a doubt after offering the act of worship doesn`t undermine its validity. And Allah Knows Best.