This'll be easy enough for us to fit into the 'better parent support' piece of the project which is slated for a few months from now. Just to make sure we're on the same page, the existing flow for this is a student going to Account -> Settings -> Pair with Observer. This would be a shortcut for that same flow: student going to Resources -> Pair with Observer.
Yessir! That is the current flow our families follow, and you described the desired flow perfectly! Thanks for your quick response!