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
Is it permissible to pay the expiation of an oath to a charitable party as it feeds the poor and needy such as Tkiyet Um Ali?
There is no harm on authorizing someone to handle the expiation of another to the poor and needy, since Shafiee's jurists stated that authorizing someone for the purpose of distributing Zakah, expiation and vow is permissible as stated in [Mughni Al-Muhtajj,vol.3/pp.237]. At last, the intention of the person who intends to authorize someone else suffices in this regard. And Allah Knows Best.
What is the ruling on someone who vowed to fast for two consecutive months, but failed to do so?
He is obliged to fulfill his vow by fasting for two consecutive months, but if he fails to do so then, it remains a debt on him until he either fulfills his vow, or dies. In case of his death, his guardian is supposed to fast on his behalf, or donate food from his estate in return for fasting, but if the guardian fails to do so then, it is all in the Hands of Allah.
Is it permissible for the heirs of the person who caused the accident (The Killer) to fast (The intended as an expiation for unintentional killing) on his behalf if the latter died in the crash?
All perfect praise be to Allah the Lord of the Worlds. May His peace and blessings be upon our Prophet Mohammad and upon all his family and companions.
One who dies while liable for obligatory fast, his/her guardians have the choice to either fast on his/her behalf or feed one poor Muslim for each day of missed fast. This applies to Ramadan and other obligatory fast, and since expiatory fast is obligatory, feeding a poor person for each missed day or fasting on behalf of the deceased is obligatory as well. And Allah The Almighty Knows Best.