What is the expiation for breaking fast due to being on a journey, or being sick, or being in a state of menstruation?

No expiation is due on the aforesaid categories, but they are obliged to make up for the missed fast. However, if any of them failed to do so while being able to, and the next Ramadhaan has come, then making up for those days is incumbent on him/her , and paying the ransom as well. 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.

I work for a company whose manager refuses to allow employees to leave during work hours. Do I incur sin if I secretly went out to join the congregation at the Masjid? Is doing so considered a breach of trust?

Praise be to the Lord of the Worlds.

We recommend that you pray at work to encourage your colleagues to follow suit, because whoever guides to good has the like of the reward of the person who actually does it. And Allah The Almighty Knows Best.

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).