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.
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 permissible for the young woman to turn the suitor down if she had no feelings for him?
Yes, it is permissible for her to do so.
My father passed away before my grandfather. Am I entitled to any share of my grandfather`s inheritance?
All perfect praise be to Allah the Lord of the Worlds. May His peace and blessings be upon our Prophet Mohammad and upon all his family and companions.
According to Islamic courts, you are entitled to what is called obligatory bequest (The distribution of estate to grandchildren who has either lost a parent before the death of the grandparents). Therefore, if your grandfather left such bequest for you, then take that share or else it is more prudent to take nothing. And Allah The Almighty Knows Best.