Using classic Outlook for Windows in business environments
So, it just worked. I don't know if changing the registry value above made it work, of if MS improved outlook. But I made the registry change and then just added my @icloud.com account (I did had to create an app-specific password with apple as expected). I chose "advanced options" and then "Let me setup manually" and it added no problem. So I essentially have two inboxes that are the same and I can send emails from each by changing the FROM dropdown.
Incase someone suggests just typing in a "from" address, this technically works, but it's only changing the reply-to address So an email received like this would show it's from whatever address the email account was chosen, but if the user clicks reply, it changes to the address you typed in the from field. So this is kinda wonky - especially if you're sending an email to something automated and it's looking for your actual email address, not the reply-to address.
Hope this help