If someone regularly fasts the six days of Shawwal, are they obligated to fast them every year?
A person is not obligated to fast the six days of Shawwal every year, even if they have made it a habit. However, someone who regularly performs a good deed should not abandon it as long as they are able.
What is the ruling of Islamic Law on leaving the Sunnah prayer of Dhuhr due to fatigue?
Praise be to Allah, and peace and blessings upon our master, the Messenger of Allah.
According to the general rule, a Muslim should strive to maintain the Sunnah prayers before and after the obligatory prayers (al-sunan al-qabliyyah wa al-ba'diyyah). One is permitted to pray them sitting from the outset, but if one leaves them due to severe fatigue, there is no objection to doing so. It is recommended (mustahabb) to make up (qadā') a time-bound supererogatory prayer (nafl mu'aqqat) at any time if it was missed.
Al-Shirbīnī (may Allah have mercy on him) said: "If a time-bound supererogatory prayer is missed, it is recommended to make it up according to the more authoritative view (al-azhar), based on the hadith recorded in the two Ṣaḥīḥs: 'Whoever sleeps through a prayer or forgets it should pray it when he remembers it.' This is also supported by the fact that the Prophet (peace and blessings be upon him) made up the two rak'ahs of Fajr when he and his companions overslept in the valley and missed the dawn prayer until the sun had risen [narrated by Abū Dāwūd with an authentic chain]." And Allah, the Most High, knows best.
What should a person who doubted having missed a pillar of prayer do?
All praise be to Allah, The Lord of The Worlds. The prayer of one who doubts having missed one of its pillars is valid, and nothing is due on him/her since having a doubt after offering the act of worship doesn`t undermine its validity. And Allah Knows Best.
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]