Ok so after a lot of messing around I found the outgoing server port number was different in the same window but through a different path (keep reading for that to make sense lol )
First, and many times, I went to TOOLS >> Email Accounts >> View/Change Emails Accounts >> Clicked on more settings...the port numbers were correct.
Where the outgoing server port was wrong was through this maze... Tools >> Options >> Mail Setup >> Send/Recieve >> Edit >> Click on Second Accounts Name >> Account Properties >> Advanced Tab >> I found that the outgoing server number was different than if I went to that same window through the first set up instructions I mentioned earlier. I found that odd.
I know I had checked that several times because the error message Outlook was giving me said to check my port numbers. This still didn't do anything until I tried restarting Outlook. Sooo, I don't know. Everything seems to be working fine now after a few tests.
I will reply back if I have problems again...or should I just start a new topic?
Let me know if you have an explanation for all that.