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]
What is the ruling on fasting the six days of Shawwal?
Fasting the six days of Shawwal is Sunnah. The Prophet ﷺ said: "Whoever fasts Ramadan and then follows it with six days of Shawwal, it is as if they have fasted for a lifetime." [Narrated by Muslim]
This is because fasting one month of Ramadan is rewarded as fasting for ten months, and the six days are equivalent to sixty days, completing a full year of fasting.
What should a person do if they suffer from an incurable illness that prevents them from fasting?
A person who has an illness that is not expected to be cured and prevents them from fasting must feed a needy person one mudd (600 grams) of food (such as wheat or rice) for each missed day instead of fasting.
Allah Almighty says {what means}: "and [in such cases] it is incumbent upon those who can afford it to make sacrifice by feeding a needy person." [Al-Baqarah/184].