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.
A woman used contraceptive pills, and her menses exceeded (15) days, is it permissible for her to fast?
The maximum of menstrual blood is (15) days, but if it exceeded that due to a medication, or the like, then it is Istihadah (bleeding outside the monthly period), and in this case she should perform Ghusl (ritual bath), pray, and fast. Moreover, she is obliged to make up for the missed fasting days which exceeded her regular menses. And Allah Knows Best.
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 performing Umrah an obligation for who is capable. Is he accountable for not performing it in this case?
Umrah is an obligation once in a lifetime for every Muslim. When physical and financial ability is present, it is preferable to perform Umrah, as well as Hajj. If one can afford to perform Umrah but not Hajj, then they should begin with Umrah, especially since Hajj nowadays is not accessible to everyone who wishes to perform it. In contrast, Umrah is more open and easier to undertake. And Allah knows best.