Wouldn't you know it. I found the answer (at least for my smtp errors) right after leaving my first reply. It is at the following URL:
I hope this works for you also.
Change ssl by tsl in outgoing server Configuration and ready
SMTP (outgoing mail server) information:
Server name: smtp.mail.me.com
SSL Required: Yes
SMTP Authentication Required: Yes
Username: email@example.com (use your @me.com address from your iCloud account)
Password: Your iCloud password
Note: If you receive errors using SSL, try using TLS instead.