Can someone who begins a voluntary fast break it?
It is preferable for someone who begins an act of worship not to break it.
Allah the Exalted has said {what means}: "and let not your [good] deeds come to nought!" [Muhammad/33].
However, if a person starts a voluntary fast (nafl) and needs to break it, they are going against what is preferable, but there is no sin upon them.
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.
Is it permissible to offer mandatory prayer while sitting?
All perfect praise be to Allah, The Lord of The Worlds, and may His Peace and Blessings be upon our Prophet Muhammad and upon all of his family and companions. Standing up is a pillar in the mandatory prayer and the prayer is not valid without it unless one cannot do it. As for Nafila (supererogatory prayer), one can perform it in the state of sitting even if he/she can stand, but his/her reward is half the reward of the person who prays while standing if he/sh has no legal excuse for such an act. And Allah Knows Best.
Where should a woman following her husband or another man in prayer stand?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
If a single woman prays with a man—whether she is his wife or a non-mahram (Ajnabiyyah)—the Sunnah is for her to stand behind the Imam and be shielded by him. If the Imam is leading both a man and a woman, the man should stand to the Imam's right, and the woman should stand behind the male follower (Muqtadi). In this way, she is shielded from the Imam by the male follower and remains at a distance from the follower and his line of sight. And Allah the Exalted knows best.