What should someone consider when choosing an email hosting provider?
It's probably going to be a central part of infrastructure, so keep that in mind. You'll use it for a long time.
Interoperability and vendor lock-in. You can move on if you want to.
What are the benefits of self-hosting over using a service like Gmail?
One word: Control. You maintain control over your solution.
If you self-host, you have more control over the product.
As a hosting provider, what are some of the pitfalls of hosting email?
Reputation management. Other services that receive email have to fight a lot of spam.
Properly configure domains for MX records.
Are there any common ways email hosting is misconfigured?
Set up SPF, DKIM, DMARK.