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.
Is it permissible to sleep after the time of the Fajr prayer has begun, with the intention of waking up shortly afterward?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah.
If a person sleeps after the time of Fajr has begun, with the second adhān, then sleeping is forbidden (ḥarām) at that point, unless he is certain that he will wake up and perform the prayer within its time. And Allah Almighty knows best.
Is it permissible to give multiple mudds (portions) of fidyah to a single person?
Yes, it is permissible to give multiple mudd of fidyah to a single person, because each day of fasting is considered an independent act of worship.
Do pregnant and breastfeeding women have to fast?
Pregnant and breastfeeding women are required to fast. However, if fasting causes them harm or unusual hardship, they may break their fast but must make up for the missed days later.
If they break their fast solely out of fear for the fetus or the child, then they must both make up the fast and give fidyah (feeding a needy person for each missed day), as the benefit of breaking the fast was only for the child.