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 Muslim physician to specialize in gynecology obstetrics, and what is the ruling on working as such?
Some fields of knowledge are an individual duty while others are a collective one, and specializing in gynecology obstetrics is a collective duty. However, if there were female physicians to treat women, then there is no need for a male gynecology obstetrics specialist to look at women`s Awrahs (private parts) except in necessary situations since the jurisprudential maxim says:” Necessity must only be assessed and answered proportionately.” And Allah Knows Best.
Does wiping over one's socks during ablution permissible?
If the socks were thick, then wiping over them during ablution is permissible so long as wiping conditions are observed. And Allah Knows Best.
What is the ruling on someone who prays Fajr late, after sunrise, knowing that they wake up on time but return to sleep and do not perform it within its time?
It is obligatory to perform the prayer within its prescribed time. If someone wakes up and knows how to act, they must perform it before the time ends. If they delay it, they are sinful and must make it up. And Allah Knows Best.