Well, although the symptoms were similar the cause doesn't seem to be the same. I held a 150nF cap across the ground and nRST pins through a number of power cycles and got the same behavior as yesterday.
The only way to get the pedal to consistently power up is to unplug the Ojai, unplug the OWL, replug the OWL, replug the Ojai. I assume what's happening is when I replug the OWL something is discharging, allowing the chip to properly detect power. It's not the end of the world, but if anyone's got a better solution I'm all ears