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Had a similair scenario,quickly resolved with a new gear drive starter,as well ipr o rings and now its immediate fire up on a 240k motor.A slowly wearing down starter is ever so gradual.Checking fuel pressure while cranking is important info to have at this point.Good luck
Had replaced the green o rings previously,if they're not sealed properly they will leak fuel out into the valley.Any signs of fuel leaking?Seems as fuel psi is good and the primary concern might be the hpop side of it not building enough pressure for the injectors.Thats what mine did before i replaced the ipr o rings,and afterward,started on the first crank.
I would say to look at either the starter not spinning fast enough or HPO... Next time you go to start the truck, take the plug out of the HPOP Res and dip a straw or toothpick in there to measure how far from the top the oil is... Should be within 1/2" or so of the top. If it is lower, fill it and try to start.
After replacing o-rings on injectors it just took awhile to get air out of fuel & oil. Smoked like hell too. A couple trips down the road & all is fine. 3 seconds Max to start.
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