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.
Is it permissible to include others in the reward of one`s sacrifice?
In the Name of Allah, and may peace and blessings be upon our Master, the Messenger of Allah.
It is permissible for the person offering an Udhiyah (sacrificial offering) to include others in the spiritual reward of the sacrifice. However, it is not permissible for multiple people to jointly share the purchase price of a single sheep or goat, unless one person gifts the money to the other.
It is stated in Mughni al-Muhtaj (6/137) by Al-Khatib al-Shirbini:
"If a person includes someone else in the reward of his sacrifice and slaughters it on his own behalf, it is permissible."
It should be carefully noted that including someone else in the reward of one's sacrifice is completely distinct from offering a sacrifice on behalf of someone else. And Allah the Almighty Knows Best.
I broke my oath and am now obligated to pay the expiation for a broken oath (kaffārat al-yamīn). Would it be valid to fulfill this by inviting the poor and needy to a meal for them to eat from?
Praise be to Allah, and peace and blessings upon our master, the Messenger of Allah.
The expiation for a broken oath (kaffārat al-yamīn) is given to the poor (fuqarā') and needy (masākīn), and it must be given in the form of ownership (tamlīk) transferred to them of the required amount — namely, one mudd of the staple food of the locality, or its equivalent monetary value. It isn`t valid to invite the poor or needy to a meal prepared for them to eat from, as this does not constitute "ownership" (tamlīk) but merely "permission to partake" (ibāḥah).
Imam al-Shirbīnī (may Allah have mercy on him) said: "What is intended is that ownership be transferred to them; therefore, providing them with lunch or dinner [as a meal to eat from] isn`t valid." [Summarized from Mughnī al-Muhtāj,Vol. 5/P.50]. And Allah the Almighty knows best.
Is Zakah due on the orphan`s money?
Yes, Zakah is due on the money of the orphan.