Is it permissible to give multiple mudds (portions) of fidyah to a single person?
Yes, it is permissible to give multiple mudd of fidyah to a single person, because each day of fasting is considered an independent act of worship.
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.
Must a person refrain from eating for the rest of the day if they break a fast of a vow (nadhr) or a make up fast (qada)?
Whoever observes a vowed fast (nadhr) or a makeup fast (qada) is prohibited from breaking it without a valid excuse. If they break it without a legitimate reason, they are sinful.
However, they are not required to refrain from eating for the rest of the day, because such restraint is only required out of respect for the month of Ramadan, not for other types of fasting.
What is the Islamic ruling on one who was unable to fast and then regained the ability?
He is not required to make up the fast (Qada) even if he becomes capable of it; whether he regained the ability to fast after paying the fidya (feeding a needy person for each day of missed fasting) or before it, because he was liable for paying it in the first place, so it remains binding upon him. However, if he delayed paying it beyond the first year, nothing is required of him due to the delay. If he is unable to pay it, it does not remain as a debt upon him. And Allah the Exalted knows best.