With adding two or more emails to the “Require”, in real life scenario you can’t log in with 2 or more emails at the same time (only one), so the conditions of the rule cannot be met.
In other words, short, “Include” will function as logical ORs and “Require” function as logical ANDs.
More about how logic works behind “Include” can be read at below link:
It’ll be easier for you to create a Group and Include Emails, especially if you’d have to allow access for multiple Applications for those email addresses/users, so you just Assign a group on the Application.
It does work for me like that, despite I have more criteria such as under the Require I’ve got Country and some other configured alongside the Assigned Group in which there under the Include is Emails with different domains @example.tld.