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.

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.

What should a person who was favored from Allah with a newborn, but couldn`t afford an Aqeeqah, do?

Aqeeqah(the sheep slaughtered on the seventh day from the child`s birth) is a desirable Sunnah for the financially able since Allah, The Exalted, charges not a soul beyond its capacity. Therefore, if the father couldn`t afford the Aqeeqah before the end of his wife`s confinement, then it isn`t due on him, and if he was able to afford it later on, then it is permissible, but if he didn`t until the child reached puberty, the latter can offer the Aqeeqah himself.

Is it permissible to offer an absentee funeral prayer?

Yes, it is permissible to offer an absentee funeral prayer.