I tried to Email the Tags: Student, Parent, Director. I clicked Send, so why is the email status showing "Pending / Not Sent"?

You have selected the Tags improperly. There are not any individuals who have all of the Tags: Parent, Student, and Director. You need to select the Parent Tag, and then click the + Add More Groups. Below that box, you will be able to then select the Student Tag. Then + Add More Groups again and select the Director Tag. Keep an eye up top on the People Selected = x tally as you grow or narrow your groups. You can see how many people are in the group you have formed. If the number is very different than what you expect, it is because you are narrowing the group (by putting multiple Tags in the same box) or expanding the group (by putting one Tag per box on top of each other) when you actually meant to do the other. 

You can find more information about Tags here:  https://www.boosterhub.com/faq #/70-tips-tricks/boosterhub-academy-71-tags?from_search=150191240