I am having a devil of a time with CiviCRM email
Possibly smtp settings, i.e. authentication? 
Outside of civi, are you able to send an email to confirm your global configuration/server/mail settings are correct?

Then go to CiviCRM, Administer CiviCRM, Outbound Mail. 
Ensure your settings match the cms. Then test to an outside email address.

If all goes well, go back to civi and try your email.

If still not working, then check what version of php you have, if 5.6, then smtp settings maybe messing you up because of peer verification.