Is the father a Mahram (Non-marriageable) to his son`s mother-in-law?
The father is a non-Mahram (Marriageable) to his son`s mother-in-law, so it is impermissible for them to look at each other, or to have a seclusion (Khalwah).
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.
My headcloth is causing me a terrible headache and severe shortsightedness. Is it permissible for me to take it off?
All perfect praise be to Allah, the Lord of the worlds. I testify that there is none worthy of worship except Allah and that Muhammad, sallallahu ‘alayhi wa sallam, is His slave and Messenger.
If the headcloth Khimar is harmful, it is sufficient to wear the Niqab (face-veil). However, with the passage of time you will get used to the Khimar and these symptoms will go away. And Allah The Almighty Knows Best.
Is it permissible to trim the eyebrows if they become excessively long?
Trimming eyebrows is permissible if they become excessively long, yet; it is reprehensible. And Allah Knows Best.