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 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 for the woman who is observing Iddah after her husband`s death to sit with her daughter`s suitor, although their marriage contract hasn`t been concluded yet?
All perfect praise be to Allah the Lord of The Worlds. May His blessings and peace be upon our Prophet Mohammad and upon all his family and companions.
A suitor who hasn`t concluded the marriage contract isn`t a Mahram*, so he must be treated as such. And Allah The Almighty Knows Best.
* The period a woman must observe after the death of her husband or after a divorce, during which she may not marry another man.
* In Islam, a mahram is a member of one's family with whom marriage would be considered haram, concealment purdah, or concealment of the body with hijab, is not obligatory; and with whom, if he is an adult male, she may be escorted during a journey, although an escort may not be obligatory.
A man who was on travel prayed Duhr as four Rakhas upon leaving Tafilah heading to Amman. However, on his way to Amman, he prayed Asir as two Rakhas (Shortened). Is what he did correct from an Islamic perspective?
All perfect praise be to Allah, The Lord of The Worlds. May His blessings and peace be upon our Prophet Mohammad and upon all his family and companions.
What he did is correct; he is liable for nothing before Allah The Almighty, since combining and shortening prayers during travel are two separate concessions. Therefore, it is permissible for a traveler to shorten prayer without combining it with another. And Allah The Almighty Knows Best.