If someone regularly fasts the six days of Shawwal, are they obligated to fast them every year?
A person is not obligated to fast the six days of Shawwal every year, even if they have made it a habit. However, someone who regularly performs a good deed should not abandon it as long as they are able.
Who is "the poor" entitled to receive Zakah (obligatory charity)?
The poor is the one who has neither money nor a source of living, or has either of them, but it isn`t sufficient such as being in need for a hundred/JDs, and having an income of forty/JDs only.
What should a person who doubted having missed a pillar of prayer do?
All praise be to Allah, The Lord of The Worlds. The prayer of one who doubts having missed one of its pillars is valid, and nothing is due on him/her since having a doubt after offering the act of worship doesn`t undermine its validity. And Allah Knows Best.
Is it valid for the 'aqīqah to be performed using the newborn child's own wealth?
All praise is due to Allah, and may peace and blessings be upon our Master, the Messenger of Allah.
It is not permissible for the guardian to perform the 'aqīqah using the newborn child's own wealth, because the 'aqīqah is a voluntary act of giving (tabarru'), and a guardian is prohibited from making voluntary expenditures from the child's wealth. Should he do so, he becomes financially liable for what he spent. And Allah Almighty knows best.