What is the ruling on praying behind a disliked Imam?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
It is mildly disliked (Makruh Tanzihan) for a man—other than the permanent designated Imam (Imam Ratib)—to lead people in prayer if the majority of them dislike him due to a religiously blameworthy reason (Amr Madhmum Shar‘an), such as associating with open sinners (Fussaq), for example. As for the followers who dislike him, the prayer behind him is not disliked for them. However, if less than the majority dislike him, or if the majority dislike him for a reason that is not religiously blameworthy, then his leading the prayer is not disliked. And Allah the Exalted knows best.
What is the ruling on wiping the head during ablution from behind a barrier like a headscarf (hijab)?
The obligation in ablution is to wipe some of the head; it is not a condition to wipe all of it. As for one who has a turban or headscarf on their head, it is permissible for them to wipe over it after wiping a part of their head in any place. This is easily done at the front of the head. This means the woman begins by wiping the front of her head from under the headscarf, then completes the wiping to the back of the head from over the headscarf. If the woman wipes over the headscarf on her head and the moisture reaches the scalp or some hair within the boundaries of the head, it suffices for wiping the head. 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.
Is it permissible for an elderly person, a pregnant woman, or someone with a chronic illness to pay fidyah before Ramadan begins?
It is not permissible for an elderly person, a pregnant woman, or someone with a chronic illness to pay fidyah before Ramadan begins.
Additionally, it is not allowed to pay fidyah for more than one day in advance, because fidyah is a substitute for fasting, and fasting is not yet obligatory at that time.
However, it is permissible to pay fidyah for a single day in advance, by analogy with paying zakat up to one year in advance.