1. I often want to email only some students, e.g.,those missing an assignment. Your current system, where I individually trash then confirm the trash is poor design: unnecessarily time-consuming. A list of names with check boxes, headed by "Select All" checked by default, would be a better (and quite common) design.
2. The gradebook is organized by last name. The email list by first name. I would prefer to have a filter choice for looking at lists of names by first or last name, so as to make looking from one to the other list more efficient.