Carb Fuel Evaporation?
I live across the river from you and yes this is an issue with the fuel we get here in the NW. Today fuel is design for EFI and Emissions and formulations change from winter to summer. My F-150 I had to crank quite a bit to get it to start after sitting months at a time outside. My Dart, not so much, it lives in the Garage but the Holley I have on it will slowly evaporate the bowls dry from sitting with a spacer, bowl shields and heat barrier coatings on the carb. I have an Edelbrock mechanical pump only and honestly, it moves fuel pretty well and even after a month of sitting only a few turns and I have fuel to fire. I have a Dakota starter which I think turns the motor over faster too, that helps the pump.
If going electric, look for one like this where it states "This model does not have a one-way check valve or an anti-siphon valve, so fuel can be pulled in either direction when the pump is turned off"
Mighty Mite 12-426 25 GPH Holley Mighty Mite Electric Fuel Pump, 1.5-4 PSI