So the last few months I have been messing around with getting the actual PCB populated with all of the components and such. Things did not go well. While I was trying to make the weird voltages I couldn't figure out why the correct voltages weren't coming out of the LT1945. Of course I thought the chip might be at fault, not my own incompetence. In the process of desoldering and replacing the chip I ripped up a few traces off the board. This is a 10-pin MSOP package....fixing this wasn't possible.

I found out what the issue was though. Shoulda just looked at the dang datasheet....

Why it didn't occur to me check for an enable pin this device. Lesson learned - read the dang datasheet.

Long story short. I had to desolder all of the components from one PCB to another PCB - thus destroying more components with tiny little legs in the process -_- . Below you can see the resulting carnage and product of my endeavours.

The Second PCB with all of the components transferred onto it

The original pcb with all of the nasty desoldering carnage

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So after all this my conclusion is... Start a new PCB. There has been some development with ESP32 and e-ink interfacing so I don't think it makes much sense to keep battling a board that will be outdated before it is even working. 

Within the next few weeks I will be starting a new PCB centered around the ESP32. It will be harder better faster stronger etc. Until then - check yah later.