After I had prayed, I found a drop of menstrual blood and was unsure when that happened; what is the ruling on my prayer and fast?
All praise is due to Allah, peace and blessing be upon the Messenger of Allah.
Your prayer and fast are correct ,and you should not make up for them, and we ask Allah, The Almighty, to duely reward you for these acts of worship. Your menses start once you see blood because the situation remains as such unless there is certainty or predominant conjecture, as per the Fiqh maxim: "Certainty is not removed by doubt". And Allah Knows Best.
Is washing both openings (Istinjaa`) a must before every ablution?
Washing the front and back openings (Istinjaa`) is a must in case they have an impurity, but if they do not, there is no need for that, and Istinjaa` is not a condition for the validity of ablution.
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 should a person who doubted having missed a pillar of prayer do?
All praise be to Allah, The Lord of The Worlds. The prayer of one who doubts having missed one of its pillars is valid, and nothing is due on him/her since having a doubt after offering the act of worship doesn`t undermine its validity. And Allah Knows Best.