One more time do a wet compression check. If ok, go back to the starter and ensure it is spinning fast enough to get you the compression you need. Personally, I'd think 200 psig loss on all cylinders being caused by a bad valve or two, slightly amiss is a SWAG. If you flunk the wet test, take it out and work it hard for a couple of hours and back off it starts to overheat to the point where it quits.
Is your starter a 5" diameter. Have you had your battery load tested such that at 200 amperes of current you maintain at least 11v at the battery terminals? Have you tested the voltage at the starter power terminal to STARTER CASE and had at least 10v during cranking? If you fail any of these tests, they go after your starting system.
After sitting on the side lines and reading all this, I don't know what other bases are left uncovered. You have done an extremely thorough job and the problem is still there........apparently you are looking in the wrong place for the smoking gun.
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I bought a 3000 years ago that the salesman had to use ether to start it in April, in Texas! It was my first diesel and was an education. The $3500 got my attention but had I known what was in store (he surely did....was a tractor roller) I would have passed on it. The problem with this tractor was that the PO had worked it really hard for it's 4500 roughly hours and there was no hose between the oil bath air cleaner and the intake manifold.....top end was shot.
Other thing I found out later was the it was running a gasser 4" starter and diesels require a 5" diameter. Then the connecting wires from the battery to the starter were old and frayed with bad connections. Then the battery wouldn't properly load test. Then I found that the starting solenoid was pitted and wouldn't carry the proper current.
So getting through all that I was in pretty good shape but not quite there.
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Moving on I realized that an overhaul was necessary. Getting into it, found that the pistons were shot where the rings ride so I had to have new pistons, rings, inserts, got mains anyway and rod bearings. Had the guy work the head over...don't remember what he did but he was recommended by the local Ford house so I used him. I did tell him to do what ever it needs and that included resurfacing.
I did a rough check of the cylinder walls and they were close enough so I was able to continue with my "in frame". I did the ball 30 degree cross hatch hone. After I got it all back together and injectors bled and all that, it fired right up. I took it out and worked it hard for awhile, several hours, watching the temp gauge for overheating which it didn't.....had it done that I would have backed off till it cooled down and do it again.
Have had the tractor now for about 15 years. Have put about 1500 hours on it since the OH. Nar a problem. Didn't even go back and tweak the valves. Passes the start in the Texas winters usually with no thermostart pre heater slobber. I do have a good size 31 battery.
In summary I think two things may help you that are herein.......go out and set your rings and ensure your starting system is up to par.
Good luck and I compliment you on your thoroughness,.
Mark