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 for a young man and a young woman to enter into a covenant as a married couple without having a true seclusion (Khalwah) until their marriage contract is officially concluded?
The relation which isn`t based on a marriage contract is forbidden, and entering into a covenant as a married couple is unaccounted for and is from the evil suggestions of the devil.
Is it permissible for an elderly person, a pregnant woman, or someone with a chronic illness to pay fidyah before Ramadan begins?
It is not permissible for an elderly person, a pregnant woman, or someone with a chronic illness to pay fidyah before Ramadan begins.
Additionally, it is not allowed to pay fidyah for more than one day in advance, because fidyah is a substitute for fasting, and fasting is not yet obligatory at that time.
However, it is permissible to pay fidyah for a single day in advance, by analogy with paying zakat up to one year in advance.
Which is better for a traveler: fasting or breaking the fast?
Fasting is better, unless it causes hardship—in that case, breaking the fast is better.