Is the father a Mahram (Non-marriageable) to his son`s mother-in-law?

The father is a non-Mahram (Marriageable) to his son`s mother-in-law, so it is impermissible for them to look at each other, or to have a seclusion (Khalwah).

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 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.

What is the ruling on having brotherly ties between a strange man and a strange woman, and is the former considered a Mahram (unmarriageable) to the latter?

Such a relation between a strange man and a strange woman is forbidden in Islam because it involves forbidding what Allah has allowed by marriage, and allowing what Allah has forbidden such as looking and the like. Such a relation doesn`t render any act lawful between them, thus they are forbidden to look at each other, have a Khulwah (seclusion), and travel together.