I appreciate the original post was written in 2014 but I want to write my theory for his symptoms, and its a lot less dramatic than leaking CSF.

I believe darrena experienced a build up of tension headaches that resulted in his thunderclap headaches probably as a result of forward head posture or upper crossed syndrome.

Usually feel pretty good in the morning and the issues start in the early to mid afternoon.

If it were something more serious why would the symptoms start in the afternoon? I would imagine he'd sat at a desk or computer with a forward head position / poor posture. The average head weighs 5.4kgs. So if your head sits 5 cm forward from mid-line your head effectively weighs 10kg more (For every inch that the head shifts forward from mid-line, the effective weight on the neck increases by 10 pounds.)

Bending over aggravates the pain/pressure feelings.

The weight of his head has already caused tension in his trapezius muscles and or suboccipital muscles . The strained trapezius and muscles cause tension headaches in the side of the head, the temple, around the ear and jaw, and upper teeth a process known as referred pain from trigger points.

Sometimes just turning my head a certain way aggravates it.

This suggests to me tension in the neck as a result of sub occipital muscle tension.

Electrical shocky type shooting pains in head that come and go randomly.

This sounds like possible occipital neuralgia type symptoms.

I enclose a couple of links that show the location of headaches caused by trapezius and sub occipital muscles trigger points. I can't find a link of the pictures only, but the websites provide good information too.

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As I say this is only a theory, but a far more likely explanation than leaking CSF.