Stop in for a cup of coffee

And it does not matter what size or shape the tank is (a tank is a tank and your water and air will take shape to the shape of the tank and air is lighter than the water) it has a top and the air even if pumped from the side will be at the top. I know you know all the principles of displacement even better than me. But it helps me explain what is going on. If your pump keeps running and you have no to little pressure your tank is water logged. Now you need to find out why.
As said, I had air pressure holding with no water coming out. In your tank, you have an outlet near the bottom. In a horizontal that outlet is midway on the side. If bladder is working, it's going side to side, not up and down working with gravity. If it is busted, then the tank is just open inside. So I would be very limited on the air space above the gravity drain line, where you have more like 95% that can drain and fill with air... I will try what you said and pump the pressure up. Also want to do some tapping and verify where the water is at.
How does the regulator work? I know you need to mess with it when priming, but after that it says to get max flow. It's so much water coming out it's tough to say if I set it right...This has the ejector in well. Foot valve, but no other check valve as far as I know.