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.
When is supplication (du‘a) more likely to be accepted: before or after breaking the fast in Ramadan?
Du‘a is accepted at all times, and this is part of Allah’s mercy and generosity toward His servants.
The Prophet ﷺ said: "No Muslim makes a supplication that does not involve sin or severing family ties except that Allah grants them one of three things: either He grants their supplication immediately, or He stores it for them in the Hereafter, or He averts from them an equivalent harm." [Narrated by Ahmad]
However, in Ramadan, du‘a is especially likely to be accepted shortly before breaking the fast.
The Prophet ﷺ said: "Three supplications are never rejected: the supplication of a fasting person until they break their fast, the supplication of a just leader, and the supplication of an oppressed person. Allah raises it above the clouds, opens the gates of heaven for it, and says: ‘By My might, I will surely grant you victory, even if after a while.’" [Narrated by Al-Tirmidhi]
Is it obligatory for someone traveling by plane in the afternoon during Ramadan to fast?
Anyone who intends to travel after dawn must begin the day fasting and continue with the intention of completing their fast, as fasting was obligatory upon them before traveling.
However, if they experience unbearable hardship after starting their journey, they are permitted to break their fast due to that hardship, not merely because of travel. In such a case, they must make up for the missed fast later.
What is the Islamic ruling on one who was unable to fast and then regained the ability?
He is not required to make up the fast (Qada) even if he becomes capable of it; whether he regained the ability to fast after paying the fidya (feeding a needy person for each day of missed fasting) or before it, because he was liable for paying it in the first place, so it remains binding upon him. However, if he delayed paying it beyond the first year, nothing is required of him due to the delay. If he is unable to pay it, it does not remain as a debt upon him. And Allah the Exalted knows best.