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My '66 with a stock 300 six and carb is a bear to start when I've left it sit for a few days or more.
When I'm driving it daily, it will start with a pull of the choke in the morning and then IT LITERALLY FIRES BEFORE THE KEY MAKES CONTACT when warm; just kidding, it starts with just a touch of the key.when warm.
But if it sits, I've tried several methods: one pump, choke; several pumps, choke; one pump or several pumps, half-choke; same as before, NO choke; same as before, choke and foot to the floor, etc.
Haven't figured out the proper procedure, and it seems that as I try different methods and let the starter cool down between attempts, it will finally fire with FOOT OFF gas and FULL CHOKE.
I have not rebuilt my carb yet, I figured that would be a winter project.
I have not checked timing, I figured that was spot-on, based on how well it runs when warm, and no pre-ignition during normal driving. I don't want to mess with that.
Could my carb be going dry (float bowl) when it sits, and it's taking that long for the fuel pump to prime it back up?
It sounds like the fuel pump is bleeding back. I would disconnect the line to the carb and pull the coil wire and crank it over. See if it takes a while to get fuel at the carb end of the line. You might get a carb kit, so you could take the top off the carb to see if the float bowl is empty. I really think the fuel pump is your problem.