Just wanted to provide an update.
The truck has started and ran since my original post. It does seem that the problem is getting much worse though. I only got it to start 3 times before it did not start for 12 hours+. Again, the truck used to give me 5-6 starts before it would just sit and crank. I could swing the key back and forth for 5-10 minutes before I would hear the fuel pump prime, and it would fire up and repeat the whole process over. Not the case anymore.
Went ahead and just purchased a GM Genuine (ACDelco) oil pressure switch and put it in on Sunday. Did not seem to fix the problem. It did seem to normalize my oil pressure gauge a bit. Before it was a little jumpy/glitchy. Could be a placebo effect, but hey I'll take it. Lol
Got the truck to start up yesterday morning, so I went ahead and drove it straight down to a family friend who knows vehicles and owns his own shop. He is going to look into the electrical aspect of the fuel pump. He was also suspecting the spider injector. If the fuel pump electrically checks out. He said he will be removing the intake today to determine if the spider needs replaced.
I noticed this time driving it, upon acceleration it had the slightest hesitation when keeping a steady throttle. I was going down the highway around 45-50 MPH, and the truck felt like it had the slightest bit of bog in it. I could even see my RPM's ever so slightly bogging down when I would feel it.
I will keep this thread updated as the information comes. Hopefully we can finally put this problem to rest. I love this truck and just want to trust it again.