The problem with this setup is that if I want to send email to [email protected] and example.com is actually handled by Outlook, I need to somehow know beforehand that email to example.com needs that special routing. Or do you just route ALL your outbound email through Outlooks MSA?
Pretty easy to tell whether example.com uses outlook; it'll have MX records pointing there.
You can usually figure that out by checking the MX records (though some spam filtering middlemen might make that hard to detect) and TXT records (if a domain imports Outlook's SPF list, it's probably on Outlook in the back).