Could my headaches be related to needing new glasses prescription?

Elbow problem. The ulnar nerve supplies the little and ring finger with their sensory supply it passes just behind the elbow joints try not to flex your elbow, do not rest the elbow on arm rests.
Unlikely. Eye strain headache is unlikely with shortsightedness, with longsighted ness (hypermetropia) it can occur after prolonged reading or close work.