Not certain I really understand the issue you are having. Both the links require a login so I can not see the directories you’ve setup.
The one thing I can answer, that is, If I understand the question. A WP User and a Connections entry is a one to one relationship, not a one to many. Meaning a WP user may only update/edit one Connections entry (the one to which they are linked to).
And… an entry can be assigned to an unlimited number of categories.
Hope this helps!