Would be no issue if he had UAS Remote Pilot Open Category - [UAS-OPEN-A1+A3] certificate; its a pain but worth getting it. Stay Legal, penalties can be severe.
A private prison has opened a large immigrant detention center in rural Michigan. I plan to photograph a rally against the detention center on Friday. The problem is that the center itself is in the woods, and not visible from the public road...
You need to CAREFULLY examine the Laws in the area and the FAA Regulations for flying near a place designated as "Critical Infrastructure" I would also look to make VERY SURE that no TFR's are put in place!! You can almost guarantee there are...