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.
Is permissible to buy/sell with non-Muslim?
Yes buying/selling for a Muslim with non-Muslim is permissible as regards what is lawful.
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 it permissible for a woman to use a contraceptive without telling her husband although he wants to have as many children as possible and she can`t care for them?
All perfect praise be to Allah, the Lord of the Worlds, may His Blessings and Peace be upon our Prophet Mohammad and upon all his family and companions.
If the pregnancy is harmful to the woman, it is permissible for her to use a contraceptive; however, this has to be backed by a medical report from a God-fearing doctor. In addition, you had better inform your of what you are doing to avoid dispute. And Allah The Almighty Knows Best.