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 on performing the Witr prayer as a single rak`ah?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
It is permissible to perform the Witr prayer as a single unit (rak‘ah). It was narrated from Ibn ‘Umar that a man asked the Messenger of Allah ﷺ about the night prayer, and the Messenger of Allah ﷺ replied: 'The night prayer is offered two by two (mathna mathna). If one of you fears the approach of dawn, let him pray a single rak‘ah to make what he has prayed odd-numbered (Witr) for him.' (Related by al-Bukhari & Muslim)). However, limiting the prayer to only one rak‘ah is considered 'contrary to the preferred way' (Khilaf al-Awla).
It is stated in Al-Minhaj al-Qawim Sharh al-Muqaddimah al-Hadramiyyah (p. 137): 'The minimum of Witr is one rak‘ah, but limiting it to that is contrary to what is best.'
The most complete form of Witr is eleven units, while the minimum level of 'perfection' is three units. It is stated in ‘Umdat al-Salik (p. 60): 'The minimum of Witr is one rak‘ah, and its maximum is eleven, performing the taslim (salutation) after every two units. The lowest level of perfection is three units with two separate taslims (meaning 2+1).' And Allah the Exalted knows best.
Is it a condition for the mosque where I‘tikaf is performed to hold Jumu‘ah prayers?
No, it is not a condition for the mosque where I‘tikaf is performed to have Jumu‘ah prayers. However, if a person vows to perform continuous I‘tikaf, and Jumu‘ah occurs within that period, then they must observe I‘tikaf in a mosque where Jumu‘ah is held so that they do not break their continuity by leaving for Friday prayer.
Which is better for a traveler: fasting or breaking the fast?
Fasting is better, unless it causes hardship—in that case, breaking the fast is better.