[mrighele]

Not OP, but I self host a few domains.

I was worried about not being able to send emails, but is seems that as long as you setup properly SPF/DKIM/DMARC you're fine. You may have problems if using a domestic address though.

For the configuration, the best bet is probably to use a product that makes it easy to configure the above three, there are a few alternatives around, like Stalwart [1] or docker-mailserver (which is little more that your postfix/dovecot/rspam combo packaged in a container) [2]

[1] https://github.com/stalwartlabs/stalwart

[2] https://github.com/docker-mailserver

[DarkUranium]

How did you manage to get Hotmail/Outlook to accept your email?

I got everything setup correctly, but Microsoft seems insistent on silently dropping my email.