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I'd fill the pri bowl via the bowl vent till it dribbles out the site plug then let er rip

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That is the plan... however I don't want to have to do that every time the car sits a month. Should I pull the carb and let it sit on the bench and watch for leaks?

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Carter and edelbrock carbs are notorious for this, but I think holleys are much better. You could run an electric fuel pump.

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I don't think it is pump related. Rear bowl had fuel, front bowl did not. I have not noticed any external leaks, so I am assuming it was leaking inside the intake.

If it was an evaporation issue, I would think that the rear bowl would be empty too after this period of time?

Been reading that a pinhole in pump diaphragm or damaged power valve can cause this (possibly)?