> [Edit] My point is that it's not hard to set up an artisan mail system; what's hard is that you create a job for yourself that is at the same time networking, user-facing, and technical. It's an interesting learning point, and I recommend it. But don't underestimate what you are taking on.
This. So much this.
I will happily run my "artisinal" mail system for myself. Would I put customers on it? Oh, hell, no.
I, sadly, always recommend that companies pay money to Microsoft for email. You are really paying for the customer support service rather than the email service.
Microsoft's email behaviour seems like anticompetitive abuse - you can whitelist an address and they overrule you and block incoming email for obscured reasons.
Customers still have problems occasionally _sending_ email to one domain, which is over 15 years old and sends <1 email per day. If they initiate and email us we can't send them a reply (if they're on MS email, sometimes). We use an outlook.com email nowadays as a relay and have to treat MS using customers differently still despite using a relatively large supplier.
Some years ago, I was lead to believe, you could pay a third-party to add you to what was effectively MS's whitelist.
Aside: back then I was doing some webdev and supporting IE5+ so I already hated MS about as much as one could.
Never paying to enable interoperability that is part of being a reasonable web citizen/company. Paying them just reinforces the negative behaviour.
Please don't recommend to people to pay money to have all their email communications read and stored by Microsoft, the US government and possibly other parties.
There are plenty of other email providers which are worth considering, and I'm sure some of them have half-decent customer support.
This. So much this.
I will happily run my "artisinal" mail system for myself. Would I put customers on it? Oh, hell, no.
I, sadly, always recommend that companies pay money to Microsoft for email. You are really paying for the customer support service rather than the email service.