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.

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.

Is it permissible to repeat the Istikhara (seeking guidance) prayer, and is it a condition that one should sleep after offering it?

All perfect praise be to Allah,The Lord of The Worlds                                                                                                                                                            Istikhara is offered once, but it is permissible to repeat it, and sleeping after offering it is not a condition for its validity. And Allah Knows Best.

How many Rak`ahs (unit of prayer) are offered in Witr prayer?

All perfect praise be to Allah, The Lord of The Worlds                                                                                                                                                                  Witr (an odd number prayer performed between Isha`a and Fajr) is offered with a minimum of one Rak`ah, and a maximum of eleven, but offering three Rak`ahs is the minimum of its complete form. And Allah Knows Best.