Is it permissible for the doctor to uncover the hair of a female patient out of necessity?
It is only permissible for him to do so when there is no female doctor, and he should examine the patient in the presence of one of her Mahrams (unmarriageable kin).
What is the ruling on a person who isn`t able to fast due to old age, or an incurable disease?
Paying the ransom is due on such a person, and that is giving a Mud (600 grams) of wheat, or rice, or the price of that amount to a needy Muslim for each missed fasting day. And Allah Knows Best.
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 to pay the expiation of an oath to a charitable party as it feeds the poor and needy such as Tkiyet Um Ali?
There is no harm on authorizing someone to handle the expiation of another to the poor and needy, since Shafiee's jurists stated that authorizing someone for the purpose of distributing Zakah, expiation and vow is permissible as stated in [Mughni Al-Muhtajj,vol.3/pp.237]. At last, the intention of the person who intends to authorize someone else suffices in this regard. And Allah Knows Best.