Well here is an update. I swapped in the Carter pump and the car ran like a champ for the past month or so. However, I was driving home from work last week and she up and died on me once again. I got the car to restart once and got to a side street where it died for good.

It was the same old symptom. I am just cruising along at 45 mph and you can start to feel the motor lose power and start to surge before it cuts out. Fuel filter was squeaky clean and I did verify spark while the car was dead. Next day, it fired up and I ran it long enough to move it to a good spot in the garage.

I put the Holley pump back on and I went through the carburetor to make sure all was fine. I did find a super cracked vacuum plug that was whistling and fixed that. I am guessing I had at least somewhat of a vacuum leak but I know that's not really my issue. Small tear in the vacuum secondary diaphragm as well so I have one of those on order. I also noticed I have the lightest (white) spring which seems kind of weird so I ordered a set of the springs to tune this later. Otherwise the carb was fine inside.

I did some diagnosis on the Carter pump and noticed that you can blow and suck air through the pump which shouldn't be possible if I understand how these work. I disassembled it and the pump was clean inside but one the valves in it doesn't seem to quite seal where you can get air to go through it both directions.

I'm not sure what my issue is but I swear I have the worst luck with this car sometimes.

Thanks for the help so far guys! I will keep everyone posted!