#1 Cylinder seems dead.

You got fuel to the top of the sight plug? you got pressure issues or a bad needle seat. I never liked the adjustable regulators. How do you have it plumbed, In the bottom and out the side with a gauge on the other side? IIRC you loosen the adjuster to lower the pressure. Car is not going to isolate a runner by itself, there has to be a valve train issue...just look at #1 intake rocker while you cycle the crank. Should move equally.
Yes. Fuel is to top on Holley carb site glass. Fuel line goes into bottom of regulator. Exits on one side and gauge on other side. I will cycle the crank and watch the rockers tomorrow. Can videos be posted here?