It could be he is suffering from two rare headache types. I have hypnic headaches and chronic paroxysmal hemacrania. That can be trickier and take longer to diagnosis. It took several years and a couple neurologists to diagnosis me.

@timpowell84 how are you doing now, Tim? I recently was diagnosed with sudden high ocular pressures and "angle closure" in both eyes which can lead to glaucoma and/or blindness. I will have surgery in a few days to hopefully correct it. Did you ever receive helpful advice and treatment? I hope so. It could be that your ocular areas have some anatomical, functional or enzyme abnormalities that might help reduce your pain, if treated. Also, Indomethacin (Indocin) is the only med that mostly prevents the severe pain I was having every night, 4 times per night until it was unbearable by 4:30am. It is was much less catastrophic with Indocin, melatonin and half a cup of caffeine nightly.