qmail ssl - if cert is for domain1.org and I have people also logging in with
domain1.com, they will see a pop-up/discrepancy e.g outlook security prompt
until they accept it permanently.


I got my cert with one name, secure.domain.com, and I have all my
users point their clients to secure.domain.com for pop3-ssl/imap-ssl
and outgoing smtp-ssl.

No need to accept, since the RegisterFly certs are trusted by default
in Outlook and Thunderbird (and just about any mail client).

apache - 1 IP per domain/ssl cert, so only having one IP (name based) they
will also see an alert unless they accept it as good in their browser
certificate manager.  I could improve that by getting more IP's and more
certificates.

Correct.

So initially, I should think about my most important domain as I don't have
multiple IP addresses yet

Sounds good to me.

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