Who is the one required to slaughter the 'aqīqah?
All praise is due to Allah, and may peace and blessings be upon our Master, the Messenger of Allah.
It is Sunnah for the 'aqīqah to be slaughtered by the guardian of the newborn — the one upon whom the child's financial maintenance is obligatory — provided he is financially capable of doing so. 'Alī ibn Abī Ṭālib, may Allah be pleased with him, reported: "The Messenger of Allah ﷺ performed the 'aqīqah for al-Ḥasan with one sheep." — Narrated by al-Tirmidhī. And Allah Almighty 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.
Which is superior: The Udhiyah (Sacrificial Offering) or giving its value in Charity (Sadaqah)?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
Performing the Udhiyah (sacrificial offering) is superior to giving its monetary value as charity (Sadaqah) to the poor and needy. This is because the Udhiyah is one of the manifest symbols of the religion. Allah the Almighty says {what means}: "That [is so]. And whoever honors the symbols of Allah - indeed, it is from the piety of hearts." [Al-Hajj/32]. This is further supported by the explicit and authentic Hadiths regarding its virtue, and the fact that the Prophet ﷺ and the Rightly Guided Caliphs after him consistently performed the sacrifice. And Allah the Exalted knows best.
Is the son of the sister by breastfeeding considered a mahram in Islam, and is it permissible for a woman to go for Hajj with him?
Everything that is prohibited by lineage is also prohibited by breastfeeding. The son of the sister by breastfeeding is considered a mahram, just like the son of the sister by blood, and it is permissible for him to be her mahram for Hajj and Umrah. And Allah Knows Best.