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 performing the Witr prayer after the Adhan for Fajr prayer?
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah ﷺ.
The time for Witr prayer begins after the ‘Ishā' prayer and ends with the rising of true dawn (al-fajr aṣ-ṣādiq). If a Muslim performs it at any point within this window, it counts as performed on time.
It is also recommended to make up a missed Witr prayer at any time — whether before or after performing the Fajr prayer, or at any other time of day. On the authority of Abū Sa‘īd al-Khudrī (raḍiyallāhu ‘anh), the Messenger of Allah ﷺ said: "Whoever falls asleep and misses the Witr prayer, or forgets it, let him pray it when he remembers, or when he wakes up." (Related by at-Tirmidhī)
Shaykh al-Islām, Imam Ibn Ḥajar al-Haytamī (raḥimahullāh), says: "The time for Witr prayer is between the ‘Ishā' prayer and the rising of dawn, based on the authentic ḥadīth to this effect. If this time has passed, it is permissible for him to make it up (qaḍā') afterward." [Tuḥfat al-Muḥtāj]. And Allah, the Exalted, knows best.
What do you say about someone who stays up all night on Laylat al-Qadr but misses Fajr prayer?
Such a person has deprived themselves of a great reward. Performing obligatory acts is more beloved to Allah than voluntary acts. Fajr prayer is an obligation, and performing it in congregation is equivalent to worshiping for the entire night. So how can someone neglect it while striving for voluntary prayers?!
Is it permissible for a praying person to make supplication in each Sajdah (a prostration) of obligatory prayer?
It is permissible for a praying person, whether praying individually, or in congregation, to make supplication during Sujood (prostration) in obligatory, or voluntary prayers. However, it is disliked for the Imam to do so since he is required to spare the prayer performers any sort of hardship, unless he is leading a certain group who don`t mind him extending the prayer.