What is the ruling on performing voluntary prayers during official working hours?

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

There is no harm if  there was break time during official working hours, but if not then it is impermissible. And Allah Knows Best.

A woman used contraceptive pills, and her menses exceeded (15) days, is it permissible for her to fast?

The maximum of menstrual blood is (15) days, but if it exceeded that due to a medication, or the like, then it is Istihadah (bleeding outside the monthly period), and in this case she should perform Ghusl (ritual bath), pray, and fast. Moreover, she is obliged to make up for the missed fasting days which exceeded her regular menses. And Allah Knows Best.

How are gaps filled during congregational prayer?

A praying person is allowed to take two steps in order to fill the gap in the row ahead. If the distance was long and requires much movement, then it is impermissible for one to move to fill it because much consecutive movement (three movements) during prayer invalidates it.

Is buying shared land from someone who has taken possession of it considered halal or haram?

The shared land is possessed by the country i.e. for all people; therefore, it shouldn't be possessed/occupied save by it's guardian/owner permission,thusly it can't be possessed save by having owners' permission. Finally, buying it from a person who don't possess it is impermissible. And Allah Knows Best.