So how this is supposed to work: pressing the top left button enables the voltage regulator. The ESP starts up, sets rxd as a high output to latch the voltage reg on. By adding a transistro to the column driver it becomes truly open collector, so no phantom powering or leakage thru protection diodes. I reckon R11 being 50k should be safe enough to avoid damaging GPIO pins.
As before, please point out any obvious flaws.
@philbowles: note I took on board your point about switching the power as opposed to deep sleep.