What is the expiation for breaking fast due to being on a journey, or being sick, or being in a state of menstruation?

No expiation is due on the aforesaid categories, but they are obliged to make up for the missed fast. However, if any of them failed to do so while being able to, and the next Ramadhaan has come, then making up for those days is incumbent on him/her , and paying the ransom as well. And Allah Knows Best.

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.

Should a person feel pleased, or have a virtuous vision after offering Istikhara (guidance prayer) in order to do what he/she had offered it for?

The result of the Istikhaarah is not necessarily that a person sees something (in his dream), or feels pleased, but the most important result of the Istikhaarah is whether a person is enabled to do a given matter or not.

What is the ruling on making up for missed fasting after the second half of Sha`ban (the month before Ramadhaan)?

One is obliged to make up for missed fasting before the start of next Ramadhaan, and regardless of offering it during the first, or the second half of Shab`an. This is because the prohibition mentioned in the Hadith is for offering absolute voluntary fasting in the second half of Sha`ban. And Allah Knows Best.