So I decided to jump in and shave it last night!
This was the first time I shaved my head on my own with hair that wasn't already short enough to cut with a razor, it was a bit of a challenge to get the back of my head with the clippers but overall it was an interesting experience and oddly enough it was kind of empowering taking care of it own my own like that haha. I even received a few complements while I was out and about today too. :)
@Cave Dweller - I have a splotch of pink right now curving along the side and front of my head from the psoriasis though it's improved pretty dramatically since I shaved so thanks!
@wpruitt, SirHarry225, AJ Q-Ball, J_Scott, amatlock2778 - Thanks again for all the positive encouragement (^_^)
Update: Photo! What do you think?
(https://www.slybaldguys.com/smf/proxy.php?request=http%3A%2F%2Fi.imgur.com%2FbnfwImY.png&hash=2c27173b16d14016b514feb17fc797dd4d8b7199)