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.
Is it permissible for one who sacrifices on behalf of another, with the latter's permission, to eat from the sacrifice?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
It is permissible for one who sacrifices on behalf of another with his permission to eat from the sacrifice with his permission, and he takes his place in distributing its meat.
It is stated in Hashiyat al-Jamal 'ala Sharh al-Minhaj (Vol.5/P.262): 'If a person sacrifices on behalf of a living individual with his permission, does he take the place of that individual in distributing the meat, because permission for the sacrifice implies permission for distribution, or does it depend on explicit permission? There is room for consideration, but the former view is not far-fetched.' And Allah Almighty knows best."
What is the ruling on sacrificing a castrated animal or one with a missing tail?
Praise be to Allah, and peace and blessings be upon our master, the Messenger of Allah.
It is permissible to sacrifice a castrated sheep; as it has been established that the Prophet (peace be upon him) sacrificed:
"...two large, fat, horned, white-and-black, castrated rams (Mawju'ayn—meaning having crushed testicles)." [Narrated by Ibn Majah in his Sunan].
It is not permissible to sacrifice an animal that is missing its tail, rump, or udder due to being cut off. This is in contrast to an animal that was naturally born without a tail, rump, or udder; such an animal is valid for sacrifice. And Allah the Almighty knows best.
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.