Is it permissible to pay the Zakah to my grandmother who lives alone in a rented accommodation with bad conditions noting she had three sons.
Zakah cannot be given to ascendants (parents and grandparents). It is obligatory for her sons and grandsons to provide for her, and they would be sinful if they fail to do so. And Allah Knows Best.
I work in an accounting and auditing office, and among the clients of the office are restaurants, hotels, and supermarkets that sell alcohol. Our work is limited to collecting invoices, whether purchases, sales, or expenses, and recording them in daily books. We also review income and sales taxes on behalf of these clients.
You are more knowledgeable about the nature of your work. If you see it as assisting in wrongdoing, then it is forbidden, as Allah The Exalted Says (What means): "And cooperate in righteousness and piety, but do not cooperate in sin and aggression" [Al-Ma’idah/2]. However, if your work is merely documenting the reality, then I hope there is no sin upon you. The the pious predecessors (Salaf) used to take the tithe from the traders of the People of the Book, even if it included alcohol, after knowing the value of their goods. And Allah The Almighty 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 teh ruling on thoughtless oath?
One who swears by Allah unintentionally and isn`t determined to fulfill his oath, nothing is due on him. Allah, The Almighty, Says (What means): "God will not call you to account for thoughtlessness in your oaths, but for the intention in your hearts; and He is Oft-forgiving, Most Forbearing." [Al-Baqarah/225]. However, it is dispraised for a Muslim to swear frequently.