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.
What is the ruling on istibra' and how is it performed?
Istibra' (cleansing from urine) is recommended. It is for a person to ensure that nothing remains of urine in its passage before performing istinja'. Its method is: to clear the throat (or cough slightly), shake the penis (meaning to pass fingers along it to expel any remaining urine if needed), and walk a few steps to the extent that one thinks nothing of urine remains if walking is needed. Each person knows his own nature best. The preferred opinion is that this differs among people. The objective is for one to think that nothing remains in the urinary passage that he fears will exit later. And Allah the Almighty knows best.
What is the ruling on sending blessings and peace upon the prophet (PBUH) after the Adhan?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
It is a Sunnah to send blessings and peace (As-Salat wa al-Salam) upon the Prophet ﷺ after the Adhan and the Iqamah, for both the caller (Mu’adhin) and the listener. It is permissible to do so aloud after the conclusion of the Adhan. However, it is preferable to maintain a brief pause between the words of the Adhan and the prayers upon the Prophet ﷺ, so that people do not mistakenly assume that sending blessings upon him is an integral part of the Adhan itself. And Allah the Exalted knows best.
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.