Spot,
While I'm sure fuel pumps can slowly die, my experience has been that they work, or don't work at all. Your problem almost sounds like a float that is set improperly.
I sure would check that, but I would also make sure the fuel pump had a unrestricted supply of gas from the tank. These old truck can accumulate gobs of junk in the tank.
When you head up the hill, you are loading the engine, and this would be a perfect time for it to start using a lot of fuel.
If you can give the line all the way from tank to carburetor a clean bill of health, I sure would suspect the carburetor itself.
If you have a short flexible hose near the discharge of the gas tank, make sure it is in perfect condition. These can collapse internally and strangle the flow of fuel to the pump.
The fact that you have to use the choke to run the engine is another sign of a low float setting. Vacuum leaks are a possibility, but check the float level first.
Stuart
