When are you taking the fuel pressure reading? After it has sat for awhile or right after you shut the truck off when you get it running? Have you tested the pressure right before you try to start it cold?
I would check the pressure right after shutting the truck off, then wait an hour and check it, and once again after another hour. If you lose fuel pressure then you either have a bad fuel pressure regulator or you have a loose fitting / cracked line or some problem that allows air in the fuel line causing the fuel to syphon back to the fuel tank.
The next time you try and start it cold, turn the key to the on position and listen for the fuel pump whine to stop, then turn the key off and repeat above step 2 or 3 more times. If it is losing pressure, then doing that will build your fuel pressure back up and it will start.
Check the pressures and report back your findings.
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