"I don't really have time to teach him how to take care of his paperwork."

That's what my school does, and we also have business development support funded by SBA and the State.

You could recommend to put him on extension and explain why and what he needs to do meanwhile, to meet his next deadline. I would guess there might be some sort of crew, so there should be someone running payroll for the rest of the crew, and someone pays bills, and...