'91 2.9 Fuel Delivery issues when starting

I was hoping someone could help me diagnose an issue with my truck. I've tried everything I could find, and still don't know what's going on. 1991 Ranger 4x4 2.9l manual tranny.

When starting my truck (warm, cold, just turned off, doesn't matter), it takes a couple of key turns to start. Once started, there are no issues whatsoever, it runs just fine on idle and under high RPMs.

I've tried turning to Key on Engine Off, and I can hear the fuel pump running for a few seconds. I turn it off then back to KOEO several times, and it has no effect on starting. No matter what I try, it doesn't start on the first crank. I have to crank several times, and pump the gas pedal to get the engine to catch. I've checked the schrader valve on the fuel rail, and I've got pressure (fuel sprays out when I press on the center of the valve).
The problem started a couple of weeks ago, and it would only start on the second try, now it takes three tries. It seems to be the same issue as this other poster:
http://www.therangerstation.com/forums/showthread.php?t=160172
I also checked the fuses and relays, and found no issues there. Is it really an issue with the fuel system as I suspect, or could it be a bad starter?
What else should I check before I start throwing new parts at it?

On a similar note, are there any tips for using a fuel pressure gauge? I rented one from O'Reilly, and hooked it up and didn't read any pressure, even when the truck was running. Since Ford uses a schrader valve, I hooked up the gauge with the Ford adapter to my bike tire, and read the proper pressure, so I know that the gauge is working. I know there was fuel pressure to be read, because I could manually press the valve and get a squirt of gasoline, so I must be connecting the gauge to this valve improperly. I disconnected and reconnected several times with no effect. Any ideas on what I'm doing wrong?

Thanks so much, this community has already saved my butt on several occasions, I hope y'all can come through for me again!

Similar issue I had with my Bronco 2, and the shop found that the fuel pressure regulator had a hole in it so it was dumping fuel into the cylinders on one side flooding the engine causing smoking issues when it would finally start. I'd look into replacing the fuel pressure regulator.