The initial start is a hard one. After that the rest of the day it starts very quickly. I replaced the fuel pump and filter. It has twin tanks and I have tried the cold start in both tanks. Same issue. If you bump the starter 4-8 times and wait 20 seconds minimum each time it will possibly start. It also helps to feather the throttle 1 to 2 inches while trying to start it. The motor turns over easy, it sounds like the fuel just isn't getting in there. You cannot start the vehicle if you don't bump the starter a bunch. The starter is strong the battery is strong motor runs better than the 03 yukon we have. Why would the vehicle not like starting in AM ( even plugged in) but rest of day even if you sit for 6-8 hours Unplugged it starts like a champ? It sounds like you are trying to start the truck without gas, it picks up when you bump the starter a bunch first.
I was wondering if the fuel system is allowing it siphon back to tanks? Air leak?

I am no expert and there are so many variables with hard start issues, the one thing that is frequently over looked is spark plugs, the important other factor in combustion engines, air fuel and spark. :-)
Battery and starter are most frequent. As starters become older and worn they require more amps to crank and when the vehicle has had many hours to cool down completely it takes more amps to start. So a strong battery and a healthy starter are a must. As far as the fuel running back to tanks it is possible but more likely if it will start and then run out right away, there should always be a little fuel left in your float bowl on your carb.

It is James again. No way to edit my answer. The truck is a 1988 it is more then likely fuel injected. Therefore the fuel pump is electric and primes the system first. Lack of fuel should not be an issue unless relay is bad. You should hear pump work

I can hear the fuel pump each time after I bump the starter is it possible the auto choke on the fuel injection system is not functioning properly? Why would not enough fuel be making it to motor until after several starter bumps. Injecter issues?

The only way to really tell on inclosed injection system is of coarse a fuel pressure test. Try also to just turn on key and off again two or three times without turning starter at all. If it fires fuel may be issue. If not other.