Actually scratch that. After wasting tons of my time I found out it was in fact the power button in Windows 8 which is "broken."
Going charm bar->Settings->Power->Shut Down does not in fact cause Windows to shut down (in the true sense). Instead it is actually hibernating so when you would Shut Down and Power back on, you weren't seeing settings applied.
In order to apply changes/settings you have to actually use the Restart option.
PS - I'll add this to my list of why Windows 8 is a terrible operating system.