What is the ruling if someone wipes his head then shaves it - must he repeat it?
If a person performing ablution shaves his head after wiping it during ablution, he is not required to re-wipe his head or repeat the ablution. And Allah the Almighty knows best.
What is the ruling on someone who eats or drinks while uncertain about the arrival of dawn, then later finds out that dawn had not yet broken?
If a person does this, their fast remains valid, as it is confirmed that they ate during the night. Similarly, if someone eats while uncertain and remains unsure whether they ate before or after dawn, their fast is still valid. This is based on the maxim of Sharia Law, which states: "Certainty is not removed by doubt." Certainty, here, is the presence of night, and the doubt concerns the arrival of dawn. Therefore, one relies on certainty and disregards doubt.
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 valid to perform the obligatory prayer while sitting?
Praise be to Allah, and peace and blessings be upon our Master, the Messenger of Allah.
Standing (Al-Qiyam) while having the ability to do so is one of the pillars (Arkan) of the prayer; the obligatory (Faridah) prayer is not valid without it. However, whoever is unable to stand may pray sitting down. As for voluntary (Nafilah) prayers, it is permissible to pray them sitting even if one is able to stand, but the one sitting receives half the reward of the one who prays standing. And Allah the Exalted knows best.