Hesitating to Start

[diezelraccoon]

Still seeking answers on this with my 03 Tahoe with the 5.3 engine. I noticed at about 1/4 a tank if it’s sitting all day/nignt you go to start it and it takes a little longer for it to fire up. There’s been times the gas light was on and I was parked at an include downhill and it would not start and I had to put it neutral and let it roll to a flat surface for it to start. I’ve noticed now when it’s down to 1/4th a tank on level surface after sitting all night it does the same thing.
I do believe if I turned the key to the on position and let the fuel pump run for a few seconds before starting, it will fire up. The fuel pressure was below specs that I outlined in a previous post. I’ve already placed the fuel pump with an OEM. Still trying to figure out what’s causing this. Perhaps fuel filter or fuel pressure regulator?
Below is a link to a video of what it’s doing.

 

[swathdiver]

I cannot view the video, says private. Anyway, I think the pump is losing it's prime because of a leak, the system isn't sealed anymore.

My first look would be the pump but you said that that has been replaced. Did you replace the entire unit with the sensors and sender and such or just the pump? Did you triple check the lines for leakage?