Is it permissible for someone to make a supplication to Allah to marry an already married, or an engaged woman?
No, it isn`t, and the person who does so is sinful before Allah, The Almighty.
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.
If the menses lasted for over than 9 to 10 days, considered menstruation?
If the duration of the bleeding does not exceed fifteen days, it is all considered menstruation, even if the usual pattern changes.
Is prayer mandatory on a dying person who goes through a state of unconsciousness, then wakes up?
If he wakes up and was conscious, then he should pray the way/manner he could, but if he wasn't, then he is exempted from obligatory prayer as Allah Says in this regard (What means): "On no soul doth God Place a burden greater than it can bear." [Al-Baqarah/286].