Is it permissible to pay the expiation of an oath to a charitable party as it feeds the poor and needy such as Tkiyet Um Ali?
There is no harm on authorizing someone to handle the expiation of another to the poor and needy, since Shafiee's jurists stated that authorizing someone for the purpose of distributing Zakah, expiation and vow is permissible as stated in [Mughni Al-Muhtajj,vol.3/pp.237]. At last, the intention of the person who intends to authorize someone else suffices in this regard. And Allah Knows Best.
What is the ruling on giving Zakat al-Fitr in cash?
The default ruling is that Zakat al-Fitr should be given as the staple food of the land. In Jordan, for example, the staple food is wheat or rice, and the amount of Zakat al-Fitr is 2,500 grams per person. It is easy to give this amount of rice to the poor and needy, and this is the correct ruling according to all Islamic schools of thought.
However, Hanafi scholars have permitted giving Zakat al-Fitr as monetary value, considering it more beneficial for the poor and easier for the giver.
Is Zakah (obligatory charity) due on the Zakah money received by a poor person, and reached a Nissab (minimum amount liable for Zakah), and a whole lunar year had lapsed over having it in his possession?
Yes, the poor who possessed a Nissab for a whole lunar year is obliged to pay the Zakah due on that money even if it was given to him as a Zakah money in the first place. And Allah Knows Best.
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.