> I have a few years of experience running my own email server and I can tell you this is a major pain in the ass. When you send your email via a small email server (a server that sends a low volume of email), you will have constant issues getting mail delivered. Also, most of the issues will not be with obscure email servers, they will be with Outlook and Gmail. When you send email, you will never know if your email will be delivered to inbox, delivered to spam folder, or blackholed entirely.
I tend to disagree, due to my experiences with running a private mail server [1].
I've had one exactly one issue with Outlook/Hotmail servers over the years.
My server is quite low traffic, but it's been delivering mail reliably. How do I know? When I send mails, there's usually follow-ups.
[1] https://jschumacher.info/2021/05/running-a-private-mail-serv...