I do not have any fuel pressure gauges.
On these trucks you definitely want to monitor the pressure where the fuel enters the VP44. After you connect a gauge, do the following tests:
As you turn the ignition key to the run position (but don't engage the starter), you should see a very brief spike of fuel pressure as the fuel transfer pump (your FASS) is energized briefly.
Next, bump the starter (but don't start the engine). The fuel transfer pump should energize and run continuously for approx. 25 seconds. Ideally the fuel pressure should be between 10 to 20 psi. Fuel pressure over 20 psi can cause hard starting.
Not related to the starting problem, but you never want to see the fuel pressure drop below about 5 psi under load at full power.
The VP pump has about 100k miles on it, its a rebuild
That's getting up there in miles and the starting problem could be the result of wear.
and the injectors are factory originals from 99
I'm not sure if they're contributing to the starting issue, but with that many miles on them, I can guarantee you those injectors are worn to the point where they're not completly shutting off the flow of fuel anymore. When tested at 90,000 miles, the original injectors in my truck were already "*******" fuel from the tips well below the pop-off pressure. I mention this because you might want to go ahead and replace the injectors as a preventive measure. Again, I'm not sure if it would help or hurt the starting issue.
Best regards,
John L.