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 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, or udder due to being cut off. This is in contrast to an animal that was naturally born without a tail, or udder; such an animal is valid for sacrifice. And Allah the Almighty knows best.
Does undergoing an endoscopy during the day in Ramadan affect the validity of fasting?
Undergoing an endoscopic procedure during the day in Ramadan—whether through the mouth, nose, front private part, or back private part—invalidates the fast.
Whoever undergoes such a procedure must refrain from eating and drinking for the rest of the day out of respect for the sacred month and make up for that day after Ramadan.
"If the fidyah becomes obligatory upon a pregnant or nursing woman because she broke her fast out of fear for her child, is it obligatory from her own wealth, or from her husband's wealth?"
All praise is due to Allah, and peace and blessings be upon our master, the Messenger of Allah ﷺ.
The fidyah (ransom/compensation payment for breaking the fast) is obligatory from the wife's own wealth, and is not obligatory upon the husband unless he voluntarily chooses to pay it on her behalf.
It is stated in Mughnī al-Muḥtāj (Vol.2/P.174): "If the two [the pregnant woman and the nursing mother] fear for the child alone — such as a pregnant woman fearing miscarriage, or a nursing mother fearing that her milk supply would decrease, thereby endangering the child — then both the qaḍā' (making up the missed fast) and the fidyah become obligatory upon them, to be paid from their own wealth." And Allah, the Exalted, knows best.