Is this a system-wide role? That puts the person in every course without enrolling. Be sure to close the eye so the students won't see the person.
I've never seen the problem you describe, Matt. It's a shame you aren't doing this in 2.0 or 2.1 because they have built in permissions testing.
We here are in 1.9.4, so farther from Nirvana than you
A workaround might be to give the almost-admin the power to upload a csv file, thereby enrolling en masse.