First, I want to name that I think purchasing MemberPress and some customization of their login form would make this possible. However, we are not planning to fully utilize anything else the MemberPress plugin offers, so I am trying to determine if this is possible via another (less costly) way first.

I would like to create a login screen where the password field is listed first and is actually comprised of about 100 options or so.

Then, the username field is listed second and is unique to the user (as normal).

Finally, I need to be able to update the username/passwords via CSV upload monthly on the backend, as frontend registration is not allowed.

Like this: http://member.txdar.org/

Thanks for any suggestions!