Given…
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Could edit Jackpot’s H3 header to 20 pin, and, update V1E ESP32 with similar change? This isn’t a breaking change, and would be backward compatible.
However newly modified V1E ESP32 modules would have a pin floating if used with older (existing) JackPot boards, not sure if PCB folks here think that’s acceptable or atrocious?
Would that asymmetrical layout will provide a enough of a cue to people to minimize future instances?
Would the design still be similar enough that either the JackPot and/or the ESP32 board are compatible with other regular 2 x 19 hardware too?
Maybe change H3 header to 20 Pin by simply adding extra GND. Need to move some near by traces. Or, instead of another GND, could use this as an opportunity to breakout an extra IO pin 
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People wanting to use the V1E ESP32 in other situations can clip the extra GND pin if needed to fit their 2x19pin projects.
This doesn’t help people using 3rd party ESP32 modules. This only helps people using V1E ESP32 with JackPot.