What is the ruling of Sharia on woman shaking hands with non-Mahram man?
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.
The Messenger of Allah (PBUH) said: "It is better to be stabbed in the head than touch a woman to whom one isn`t related." [Transmitted by Al-Tabarani /Al-Mo`jam Al-Kabir, Hadith No.16880]. Accordingly, it is forbidden for men to shake hands with non-Mahram* woman. And Allah The Almighty Knows Best.
* The women/men that you are allowed to marry. It includes all women/men other than mahram (including cousins).
Is the son of the sister by breastfeeding considered a mahram in Islam, and is it permissible for a woman to go for Hajj with him?
Everything that is prohibited by lineage is also prohibited by breastfeeding. The son of the sister by breastfeeding is considered a mahram, just like the son of the sister by blood, and it is permissible for him to be her mahram for Hajj and Umrah. And Allah Knows Best.
Is my son who was breastfed one filling time by my aunt considered a brother to her children?
The baby who was suckled five sporadic times by a woman is considered a son/daughter of hers.
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.