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.
When is a child instructed to fast?
A child is instructed to fast at the age of seven if they are capable of fasting and have reached the age of discernment, by analogy to prayer. They should be encouraged but not forced, so they can become accustomed to it. It is obligatory for their guardian, whether a father or another, to instruct them.
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.
Is it permissible to pay the Fitr Zakah (obligatory charity) of Ramadan on behalf of a dead person?
The Fitr Zakah of Ramadhaan isn`t due on one who had passed away before the sunset of the last day of Ramadan. And Allah Knows Best.