Update November 18, 2016
If you are experiencing issues with outgoing email then please read this comment below and my answers. This shows how to change the outgoing server port. If port 25 doesn't work then try port 587.
In this video I walk you through setting up a WA SiteEmail account on your own dot com and configuring Outlook to send and receive emails.
First please follow Kyle's tutorial for setting up your domain specific email address Setting up a domain specific email account
Once you've set up your email account check to see if it works properly before proceeding with the Outlook setup.
I'm using Outlook 2016 but the settings should be the same for other versions of Outlook but it will look a bit different.
Personally, I'm not a fan of web-based email (webmail). Mostly because I have more than one email address and I like to check all of them at the same time without logging in and out of each account. And, yeah, having a personal email like firstname.lastname@example.org as well as email@example.com makes my business look more professional. It's another way of leveling the playing field. My little dot com looks more like a big business.
Outlook can be a bit tricky to set up new email accounts and I spent a fair bit of time sorting this one out for you. So I hope you like it.
As always, I'm here to help you.
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