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.
Is it permissible to openly announce the engagement of a woman who is in her waiting period (iddah)?
It is not permissible to openly announce the engagement of a woman in her waiting period (Iddah), but it is permissible to hint (imply) at it if she is in her waiting period after the death of her husband. And Allah Knows Best.
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 for a sick person to pray while sitting on a chair?
All perfect praise be to Allah, The Lord of the Worlds It is permissible for a sick person, who is unable to stand up, to offer prayer while sitting on a chair. If he/she was unable to prostrate while on the chair, the he/she should pray while sitting on the ground, but if he/she was neither able to bow (Roku),nor to prostrate, then he can do them while sitting on the chair. And Allah Knows Best.