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.
Is it permissible to offer Istikhara prayer (seeking guidance) after Witr Prayer (A confirmed Sunnah which is offered after Isha prayer and before Fajir prayer with a minimum of 3 Rak`as and a maximum of 11)?
It is permissible to offer Istikhara before and after Witr prayer as it is permissible at any time except that in which prayer is disliked. And Allah Knows Best.
Should a pregnant woman who broke fast because of pregnancy make it up, and is a ransom due on her?
The pregnant and the suckling, if they fear for their health, may break their fast and make up for it, and no ransom is due on them. However, if they broke fast in fear for the fetus and the baby, then they are obliged to make up for it, and pay the ransom which is feeding a needy person for each of the missed fasting days. And Allah Knows Best.
What is the ruling on swearing on the Holy Quran and breaking that oath?
It is impermissible to swear on the Holy Quran in vain, and it is also impermissible to subject it to such an act since breaking the oath after swearing on the Quran entails an expiation.