When emailing school parents I do NOT want their email addresses to show (so
no one can see each other's email addresses), yet I don't want to use Bcc (I
want the parents to see who I sent the email to, for example 'all school' or
'2nd graders'). Can I accomplish this using the 'display as' field?
Sometimes it works, but if I change a current contact not to display their
email address when testing it doesn't always work (maybe I have to re-start
Outlook to have changes take effect)?

I will also be using distribution lists to email the parents (i.e. 2nd
graders, 5th graders, etc), so maybe somewhere in there there's a way to
accomplish this?