What is the ruling on a person who broke the fast a day in Ramadan due to hardship?
He/she is obliged to make up that day.
A man break his fast once during Ramadan and he already have an expiation of fasting for two consecutive months. He fasted for a month and passed away. Is it permissible for his sons to fast the remaining month equally?
Fasting for expiation must be performed consecutively. I advise his children to feed sixty poor people, giving each one half a kilogram of rice or its monetary equivalent. This is because if a living person is unable to fast, they are required to feed sixty poor people, and death constitutes an inability. And Allah The Almighty Knows Best.
Is it permissible for a person who has to make up for missed fasts to fast six days of Shawwal (the month directly after Ramadan) before making up for the missed fasts?
Yes, it is permissible for him/her to do so, but it is better that they make up for missed fasts first. And Allah Knows Best.
Is it permissible for the man to go out wearing shorts?
All Perfect Praise is due to Allah, The Lord of The Worlds
It is permissible so long as his Awrah (private part), which is between his navel and knee, is covered. However, the regular wear traditions and modesty are to be observed. And Allah Knows Best