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Vapor Lock..

Electric or mechanical fuel pump. Anecdotal evidence suggests there is less tendency for heat soak or vapor lock with an electric pump.
 
No sight Glass old school plugs... yes i have air bleeds


Start car up, pull off sight plugs and make sure you're under the hole with fuel running nothing dribbling out, then let me know what your intermediate air bleeds you have, & idle air bleed numbers.
Set fuel pressure to 7psi.
 
You can also pull the air cleaner before you start it after a hot soak of when the problem happens and see if its wet or you see any fuel dripping before you start it. Of course without us actually hearing and seeing it we can only guess but that sounds like a hot soak problem of the fuel getting hotter from the eng heat rising after you shut the car off and pushing some fuel and fuel vapors into the eng causing it to be way rich upon a hot start. You might even want to open the hood after you park it after the drive to let much of the heat out from under the hood as if its a hot fuel soak problem that may help some. And I would take the air cleaner off after you shut it off and leave the hood open and then look down into the carb before you start it to see if you see any wetness in the carb throat from fuel. See if it starts any easier with you leaving the hood up and air cleaner off while it sits and let us know how it acts then. Ron
 
What would be your suggestion to taking care of this problem
I'd try a different carb to see if the problem goes away.
99% of the time spark/ignition is the problem but from what you've described it appears that you have fuel soaking into the manifold plenum and causing the issue.

Just my 2 cents
 
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