Is it permissible to perform Tayammum for a month due to a medical condition that requires avoiding water?

Tayammum is permissible so long as the above excuse lasts. And Allah Knows Best.

Is it permissible for a suitor to go out with his fiancé upon the conclusion of the marriage contract?

Upon the conclusion of the marriage contract, the woman becomes lawful for her husband. However, the customary practice should be observed in this regard since rights could be lost in case of divorce, or death.

What is the ruling on the cessation of blood after (40) days from delivery, but later continued sporadically during two days of Ramadan?

Once postpartum bleeding (Nifas) ceases, and the woman is certain that it won`t reoccur, then she becomes ritually pure and so she is free to make Ghusl (purificatory bath), pray, and fast. If the bleeding reoccurs before fifteen days from its cessation, and before the end of (60) days after delivery, then the ruling on postpartum bleeding is effective, and her fasting and prayer are null and void, thus she must make up the fasting that she missed and not the prayer during those particular days.

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.