Test port 443, issue the command "telnet servername.domain.com 443" to test connecting from a remote host to TCP443 on the server in question. You'll either get "connection refused" (not listening or is filtered/blocked by the server or a an intermediate device) or you'll be sent immediately to a blank window with a cursor, indicating that the traffic is routing in to that port.
For most of the queations you posed I believe the below will help:
Mac OS X 10.5: Can receive email, but not send email
When trying to send email messages in Mail, an alert similar to this may appear:
"Cannot send message using the server example SMTP
The server 'smtp.example.com' cannot be contacted on port 25.
Select a different outgoing mail server from the list below or click Try Later
to leave the message in your Outbox until it can be delivered."
See this link on Apple Site: http://support.apple.com/kb/TS1307?viewlocale=en_US
Wes