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Sounds like a bad fuel pressure regulator. I just looked at a '99 Siverado where the regulator went bad. It sits on or near the fuel rail. You need to remove the vacuum line from it and see if there is gas in the vacuum line, if yes then replace. Then apply vacuum to the regulator and see if you can draw fluid into your vacuum pump, if you can the regulator is also bad. If you think the regulator is good, then you should verify that the vacuum hose you disconnected is actually applying vacuum, if not find out where the vacuum leak is. If all this fails, then you should be looking for a pinched off or kinked fuel return line. Its the line running from the fuel rail and heading back to the tank.
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