What is the ruling on wiping over socks?
It is not permissible to wipe over most common socks today because the conditions for wiping are not met. The concession was reported for wiping over leather socks (khuff) and socks (jowrab) with conditions: They must be thick, not allowing poured water to penetrate, enable one to walk in them, be worn while in a state of purity (from ablution), cover the entire foot up to the ankles (meaning covering the protruding ankle bones), and not be torn. And Allah the Almighty knows best.
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.
Does having a wet dream during the day in Ramadan break the fast?
Having a wet dream during the day in Ramadan does not invalidate the fast. However, one must perform ghusl (ritual purification) to ensure they do not miss their prayers.
What is the ruling on one who sees moisture on his clothes and doubts whether it is semen or pre-seminal fluid (madhy)?
Whoever finds moisture upon waking from sleep and doubts whether it is semen or madhy, and cannot distinguish between them, he may choose between them and act according to his choice. If he wishes, he can consider it semen and perform the ritual bath, or consider it madhy, perform ablution, and wash what it has soiled. This is because if he fulfills the requirement of one of them, he is definitively free from it, and the default is his innocence from the other. And Allah the Almighty knows best.