Drupal - How do you add a PDF attachment to an email?
FINALLY! 4 weeks later...
So the following code ended up working for me:
$attachment = array(
'filepath' => 'sites/default/files/MyFormsOfAssistance.pdf',
'filename' => 'MyFormsOfAssistance.pdf',
'filemime' => 'application/pdf'
);
BUT, the key was that in the MailSystem Configuration I had to set the Formatter and Sender to "SMTP Mailer". MimeMail's config automatically pulled it's values from my SMTP's configuration.