not holding fuel pres. on 2002 Chevrolet Silverado 1500

have to crank 4-5 times before it will start have new fuel filter and replaced fuel pump 1 year ago

Asked by for the 2002 Chevrolet Silverado 1500
Without being able to do tests its hard to guess, but I would Tee in a fuel pressure gauge crank over the engine watch the fuel pressure, switch off the engine it should hold fuel pressure for a period of time, if it drops immediately I would pinch of the return line after the fuel rail/fuel pressure regulator and repeat the test see if it now holds fuel pressure. If it does the fuel pressure regulator may be bleeding of pressure, if the fuel pressure still drops look for a leaking injector but this would show up in a big cloud of black smog on start up, bad fuel mileage and fouling of the spark plugs.
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Try the starter or maybe the flywheel has torn Teeth