You continually mention that it seems like the fuel bowl runs out of fuel. Quadrajets were notorious for having leaky jets. When rebuilding the carburetor assemble the jets intothe fuel bowl. Then turn the fuel bowl upside down and you will find two plugs underneath the jets. These are plugs put into the fuel bowl under the jets because during the original machining process they drilled straight through the fuel bowl. Coat the plugs with a liberal helping of clear nail polish. The nail polish is fuel resistant and will seal the plugs and prevent the jets from allowing the fuel bowl to leak. The leaky jets usually allow the fuel bowl to drain after sitting overnight, but this could be part of your problem.
Take the fuel line off of the front of the carburetor. REmove the coil wire from the distributor. Have a buddy crank the engine while you hold the fuel line in an empty coffee can. The fuel should spew out of the fuel line with good flow. You should have a small pool of fuel in the bottom of the coffee can after a few moments of cranking. I know this is pretty vauge but it is a good way to test your fuel pump for flow.
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Check float needle for sticking in seat or binding float.
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Rebuild the carburetor.
Just thinking following the service manual would be a logical way of going about troubleshooting. Hope it helps.