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.

If a father stops his daughter from getting married, is it permissible for her to conclude the marriage contract herself?

It is permissible for the father to stop his daughter from getting married if there was a lawful reason for that, and she isn`t allowed to conclude the marriage contract without her guardian. However, if her father denied her right in getting married for an unlawful reason, then she should go to court.

Is it allowed to shave my beard to join the army taking into consideration that I can`t find a job?

All perfect praise be to Allah, the Lord of the worlds. I testify that there is none worthy of worship except Allah and that Muhammad, sallallahu ‘alayhi wa sallam, is His slave and Messenger.

The army should be joined in preparation for Jihad (Fighting in the cause of Allah), so if Jihad contradicts with growing a beard then it is allowed to shave it. And Allah The Almighty Knows Best.  

Is it incumbent on the fiancée to obey her fiancé?

When the woman settles in her husband`s house, it is incumbent on him to provide for her and it is incumbent on her to obey him. Before that, and if the marriage contract had been concluded, then she is lawfully his wife and thus she should abide by custom in treating him, but if the marriage contract hadn`t been concluded, then she should treat him as a non-Mahram (Marriageable).