Well, I'm back from vacation, so I am working ******* the truck today.
First, I confirmed with absolute certainty that NO smoke whatsoever is coming out of the tail pipe during cranking.
I also did 2 compression tests and got these numbers:
Cyl----Test 1---Test 2
#1-----210------250
#2-----230------140
#3-----190------120
#4-----370------320
#5-----220------150
#6-----220------150
#7-----250------220
#8-----170------160
How bad are these numbers? Would this explain the no start problem?
I am sorry to see that your numbers are so low, lets just hope that possibly you had a faulty gauge. If it were just a couple cylinders that were low, we could blame it on a head gasket or valve sealing issues, but with all of them that low, you either have a bad gauge, you did something wrong (not sure what you could mess up on to be off by that much twice) or you just have a very worn engine.
It would be great to find someone close that has a verified good compression tester that would work for your engine, that could test your engine again. I never bought one to work on my diesel because I could always use the one from the shop and it was a known good snap-on, that I could use whenever I needed.
Let me see what I could come up with, I have a good friend from high school who lives close to cincinatti in Indiana who is a diesel mechanic, let me call him and see if he has everything to test that engine and then see if it is possible for him to run over there and help you sometime, I might be able to come up there too, I would probably have to take the wife though, because his gf and my wife are friends, so I couldn't stay all day, I am sure we would have to make a trip out of it and go spend money somewhere.
But an old trick you use on tractors to rule out valve problems is to squirt a few drops of oil in the cylinder and rotate the engine over a few times then hook the compression tester up and take a reading on that cylinder again and see if the number goes up. You might want to try it and see if it will raise your numbers dramtically, if so then the cylinders are plain worn out. Don't put a lot of oil, due to the little to no clearance in these diesels. I have used this trick many times on old gas tractors but have never had a diesel with numbers so low that I every tried this.