@MPG88
I have tried configuring my Rogers Yahoo e-mail on my Mac running Outlook 2011 and was able to do that successfully.
In Outlook, Preferences and Accounts:
User name: Rogers Yahoo user name (without the @rogers.com)
Password: Rogers Yahoo password
Incoming server: pop.broadband.rogers.com
Override default port: not checked
Use SSL to connect: checked (by checking this, the port is changed from 110 to 995)
Always use secure password: not checked
Outgoing server: smtp.broadband.rogers.com : 465
Override default port: checked
Use SSL to connect: checked
More options: Authentication: Use incoming server info