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.
When is Istikharah (guidance prayer) Du`a offered, before Tasleem (saying asalamu alikum warahmatu allah wa barakatuh to end the prayer), or after it?
It is offered after Tasleem.
Is it incumbent on the fiancée to obey her fiancé?
When the woman settles in her husband`s house, it is incumbent on him to provide for her and it is incumbent on her to obey him. Before that, and if the marriage contract had been concluded, then she is lawfully his wife and thus she should abide by custom in treating him, but if the marriage contract hadn`t been concluded, then she should treat him as a non-Mahram (Marriageable).
What is the ruling on congratulating others on the arrival of Ramadan?
Congratulating others on the arrival of Ramadan is permissible.
If someone does it to express their love for worship and the blessings of Ramadan, and congratulates their fellow Muslim, they have done something good.
The Prophet ﷺ said: "Shall I not tell you something that, if you do it, you will love one another? Spread peace (Salam) among yourselves." [Narrated by Muslim]
Giving Salam is a prayer for peace and safety.