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.

Is Zakah due on the orphan`s money?

Yes, Zakah is due on the money of the orphan.

Is it permissible for the man to go out wearing shorts?

All Perfect Praise is due to Allah, The Lord of The Worlds

It is permissible so long as his Awrah (private part), which is between his navel and knee, is covered. However, the regular wear traditions and modesty are to be observed. And Allah 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).