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 for a suitor to go out with his fiancé upon the conclusion of the marriage contract?

Upon the conclusion of the marriage contract, the woman becomes lawful for her husband. However, the customary practice should be observed in this regard since rights could be lost in case of divorce, or death.

Is it permissible to offer mandatory prayer while sitting?

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.                                                                                                                                                                                                                            Standing up is a pillar in the mandatory prayer and the prayer is not valid without it unless one cannot do it. As for Nafila (supererogatory prayer), one can perform it in the state of sitting even if he/she can stand, but his/her reward is half the reward of the person who prays while standing if he/sh has no legal excuse for such an act. And Allah 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?