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 a woman in her waiting period (Iddah) after her husband's death to leave her house and mix with non-Mahrams?
It is not permissible for a woman in her waiting period (Iddah) after the death of her husband to leave her house except for a necessity, such as for medical treatment, nor is she allowed to mix with non-Mahrams. A woman is not permitted to mix with anyone other than her husband or Mahrams, whether she is in her waiting period or not. However, there is no harm in accepting condolences from those who visit and responding to their inquiries about her well-being. 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 for a Muslim woman to leave her house adorned and without wearing her proper Islamic attire?
A Muslim woman isn't permitted to leave her house adorned and without wearing proper Islamic attire. And Allah Knows Best.