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.
Must a person refrain from eating for the rest of the day if they break a fast of a vow (nadhr) or a make up fast (qada)?
Whoever observes a vowed fast (nadhr) or a makeup fast (qada) is prohibited from breaking it without a valid excuse. If they break it without a legitimate reason, they are sinful.
However, they are not required to refrain from eating for the rest of the day, because such restraint is only required out of respect for the month of Ramadan, not for other types of fasting.
Can a woman leading other women in Tarawih prayer recite aloud?
Yes, a woman leading other women in Tarawih prayer is allowed to recite aloud, as long as no non-mahram (other than unmarriageable kin) men can hear her.
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.