So once I uncommented the left/right button LCD re-init in v0.66, it will properly re-init my LCD, though I do see that the time for some reason resets when I do that - not to zero, but to somewhere between 12s and 1:37.
I also confirmed that the mpguino Game of Life has the same issue. I'm going to try to re-code the LCD class to more closely follow Yoshi's timing suggestions and see if I can kick this issue.