20psi sounds normal. The timing retardation used on the '98 year trucks, plus the loss of power through your transmission sounds like it's doing what it was made to do.... we get spoiled by the later trucks and the power they provide. Some of the suggestions above sound like what I would suggest. A TC or a pump calibration. Or both.
Disagree if you want, but computer controlled injection systems are scientifically better than mechanical. With a mechanical you are stuck at one timing setting where the computer control advances and retards it according to RPM and other inputs. Imagine an old gas engine without vacuum advance. Comparing the mileage of three different vehicles isn't much of a testament. My wife's Toyota gets 35mpg, so what?
Politely, I must disagree. Timing is controlled by the injection pump setting, yes. But, the old VE's had both static and dynamic timing, and were a marvel of engineering. The P-pumps are only static, but can be calibrated to operate at an ideal rpm range. Scientifically, the electronic managed systems SHOULD be more efficient and dependable, given the advancements in electronics and materials. Statistically, the reality is the electronic systems are more prone to failure, and rarely get much better mileage, if they do. The results are all across the charts, with some getting 20-24mpg, and others 12-16. The higher compression ratios of the newer engines help with mileage, as well, but the electronic features of the injection system wear out quicker and fail at a much higher rate. HPCR injectors are known for their failures at lower mileage. How many p-pumped 12v's, even when bumped to equal the newer HPCR's HP rating, will run well over 300k miles with little to no repairs? I've never had a HPCR run that many miles without needing an injector.... or six.... The lowest bidder war comes at a cost... to us.
And comparing three different trucks is very relevant, when each has a different version of the same engine.... it's the progression (or regression) of technology.....