Is it permissible for someone who is unable to fast to pay the fidyah (ransom/compensation payment) to himself, due to his own poverty?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah ﷺ.
It is not permissible, nor does it fulfill the obligation, for a sick person who is currently and permanently unable to fast to pay the fidyah (ransom/compensation payment) to himself, since it is a financial obligation owed by him, established as a standing debt upon him — much like any other debt he owes. If he were to pay it to himself, it would not thereby be discharged. So if he cannot find [anyone eligible to] pay it to, it remains a standing obligation upon him, and is not thereby waived. If Allah, the Mighty and Majestic, later grants him wealth, it becomes obligatory upon him to pay it out to the poor and needy.
Imam al-Khaṭīb ash-Shirbīnī (raḥimahullāh) said: "There is no difference in the obligation of the fidyah between the wealthy and the poor person; its benefit lies in its remaining established as a standing debt upon the poor person [until he is able to pay it] — and this is the more correct position (al-aṣaḥḥ), as indicated by the wording of ar-Rawḍah and its source text." [Mughnī al-Muḥtāj, Vol.2/P.174]
Accordingly: it is not permissible for a Muslim to pay the fidyah to himself while he remains poor. If the sick person is poor, he is not obligated to pay the fidyah immediately, and it remains a standing debt upon him until a time when he has sufficient means and wealth. And Allah, the Exalted, knows best.
Is an elderly or chronically ill person required to pay additional fidyah if they delay it beyond the first year?
An elderly person or someone permanently unable to fast must pay fidyah by feeding one needy person for each missed day.
However, if they delay paying fidyah beyond the first year, no additional fidyah is required.
This differs from someone who delays making up missed Ramadan fasts (qada) without a valid excuse until the next Ramadan begins—such a person is required to pay an additional fidyah for the delay.
Does Laylat al-Qadr move between the nights of Ramadan?
Laylat al-Qadr is definitely in Ramadan, and it is most likely in the last ten nights, especially on the odd-numbered nights.
For this reason, the Prophet ﷺ commanded observing worship in the last ten nights, and he himself used to dedicate those nights to worship. Many people put special effort into the 27th night of Ramadan, and they are rewarded in any case, whether they actually coincide with Laylat al-Qadr or not, because worshiping on any night of Ramadan carries great rewards.
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.