Personally, I can't reconcile having a self-hosted email server and using Outlook to access said email.

I'm being an ass in saying this, because I'm aware human motivation is a beautiful kaleidoscope of variables, but I would have guessed at the venn diagram of 'those willing to compromise and use a Microsoft product' is mutually exclusive with that of the 'I'm hardcore enough to self-host email'.

I will say, however, that Outlook used to be one of the better desktop email programs, so I'll grant some legacy lenience.