I broke my oath and am now obligated to pay the expiation for a broken oath (kaffārat al-yamīn). Would it be valid to fulfill this by inviting the poor and needy to a meal for them to eat from?
Praise be to Allah, and peace and blessings upon our master, the Messenger of Allah.
The expiation for a broken oath (kaffārat al-yamīn) is given to the poor (fuqarā') and needy (masākīn), and it must be given in the form of ownership (tamlīk) transferred to them of the required amount — namely, one mudd of the staple food of the locality, or its equivalent monetary value. It isn`t valid to invite the poor or needy to a meal prepared for them to eat from, as this does not constitute "ownership" (tamlīk) but merely "permission to partake" (ibāḥah).
Imam al-Shirbīnī (may Allah have mercy on him) said: "What is intended is that ownership be transferred to them; therefore, providing them with lunch or dinner [as a meal to eat from] isn`t valid." [Summarized from Mughnī al-Muhtāj,Vol. 5/P.50]. And Allah the Almighty knows best.
Can I start fasting based on the moon sighting of another country?
You must follow the moon sighting of the country you are in.
What is the ruling on a woman who takes medication to delay menstruation for fasting?
If a woman takes medication (to delay menstrual period) and does not experience menstruation, her fast is valid. However, she is not advised to do so unless there is a necessity.
If the medication harms her, even potentially, it is forbidden (haram) for her to take it.
Is it permissible to pay the Zakah (obligatory charity) for settling the debt of a deceased relative?
It is impermissible to pay the Zakah for settling the debt of the deceased since Zakah is paid to eligible recipients who are alive. As for the debts of the deceased, they are to be settled from the estate before dividing it amongst the heirs, but if the deceased didn`t leave an estate, then it is desirable for his/her heirs to settle those debts if they can afford them. And Allah Knows Best.