I just recently bought a truck with this issue. 1996 F-250 XLT, CCSB, 7.3L, 4X4, ZF5.

It starts briefly then immediately dies on the 1st crank. It only starts and runs on the 2nd or 3rd crank. Sometimes roughly for a second or two then smooths out. After running for a while the issue clears up sometimes but not always. it's 50/50 after that.

Here's 2 videos of it happening:

I discovered and auxiliary fuel filter/water separator on the frame rail. The hand written install date on the filter is 2014. Could this be my issue?
Picture: 20160404_091932.jpg Photo by DannyGrant_photos | Photobucket

Which leads me to:
Delete this auxiliary filter or put a new one on? It seems to me that too many filters could cause a drop in fuel pressure, right?

I also found a broken body ground strap. The truck seems not to notice its broken. Any idea what this is for?
Picture: 20160404_093055.jpg Photo by DannyGrant_photos | Photobucket

Thanks!

 

Put a new filter on but kind of sounds like it might be ipr related

I'm assuming everything is stock

 

I ordered a new filter for the auxiliary fuel filter. If that doesn't fix it, I think my cheapest route in diagnoses next is:

1.) Fuel injection ressure tester (~$100)

2.) Auto Engenuity (~$400) to test IPR, HPOP, etc

 

If you have an Android device get the Torque Pro app and a Bluetooth OBD2 dongle that will tell you everything you need to know on that and will only cost you about $25

All you need to test fuel pressure is a tire gauge

 

And if you want a more "dedicated" fuel presure gauge, you don't need to spend $100; something like this - Fuel Pressure Tester & Fuel Injection Pump Tester - will do.