Ok, got a few messages back from some friends going into the medical field:
#1: Could be a tension headache, or TMJ which is a joint problem in your jaw. Should go to a doctor to get looked at for TMJ
#2:
Could be two separate problems; headaches are often caused by vasodilation of blood vessels in the brain. Caffeine is a vasoconstrictor, meaning it could relieve the pressure and thus, alleviate the headaches he's having. Sleeping in an awkward position can cause tightness in his neck, although I don't think it would affect his face. Has he noticed any changes in vision, level of consciousness, nausea, vomiting? I'm working from a very small knowledge-base, and ultimately, the best advice I can give is to seek a medical professional if his symptoms don't resolve.
#3: AIDS.