Is it permissible for the guardian to give Sadaqa (voluntary charity) from the money of the orphans?

It is impermissible for the guardian to donate from the money of the orphans because he is entrusted with the safekeeping of that money, and is prohibited from donating it.

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.

What is the semi-circular structure abutting the Holy Kabah?

It is the Black Stone of the Holy Kabah, and one should pass from behind it while offering Tawaf (circumambulation) because it is part of the Kabah. 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?

All perfect praise be to Allah, The Lord of The Worlds, and May His Peace and Blessings be upon our Prophet Muhammad and upon all of his family and companions.

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.