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 there zakat on social security savings (retirement benefits)?
If the retirement benefits are received, zakat is due on them for one year. Before receiving them, they are not in the person’s possession to be liable for zakat. And Allah Knows Best.
What should a praying person who doubts having offered one, or two prostrations in the third Rakah (unit of prayer) do?
Whoever has doubts about their prayer should consider what is less i.e. the above person should offer another Sajda (prostration) and complete his/her prayer, then offer Sujood As-Sahw (prostration of forgetfulness). And Allah Knows Best.
Is it permissible to offer Istikhara prayer (seeking guidance) after Witr Prayer (A confirmed Sunnah which is offered after Isha prayer and before Fajir prayer with a minimum of 3 Rak`as and a maximum of 11)?
It is permissible to offer Istikhara before and after Witr prayer as it is permissible at any time except that in which prayer is disliked. And Allah Knows Best.