CARBURETOR DATED

[boloboss]

My timing was initially set at 4° and I turned the distributor just a smidge it to advance it

 

[Vbb199]

Seems like theres potential the timing could be retarded too much and its causing your issues with not wanting to start back up after being ran a while
Try 8 or 10° and see if it does it anymore

 

[boloboss]

Ok

 

[Vbb199]

That might necessitate enrichening your idle mix a little also, but perhaps not

 

[ali_c20]

I run 12 degrees on my K5 and 14 on the 66 Impala.
Always be sure your ignition system is working as it should before fiddling with the carb.

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Search Uncle Tony's Garage on youtube, this guy knows tons about carbs and ignition and all the other stuff.
He's a Mopar guy but the principles are the same for all engines.