How do you represent someone in the Users file if they are both an Administrator and a Teacher? Since only one role can be specified for a user, are you supposed to list multiple rows for the user with a different Sourcedid per row?
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I can't speak with authority
I can't speak with authority on CSV, but we have similar issues with the REST API so I can speak to how we've solved it. In instances in which a user has multiple roles (most commonly teacher+administrator or teacher+guardian) the user gets two different user records with their own sourcedId. We're not happy with the solution, but the limitations of the 1.1 API forced us to go that direction.
That said - this is a problem solved in 1.2. Users can have multiple roles in multiple orgs. It is a much better data model. If you haven't, I encourage you to check out 1.2.