Your problem does not sound uncommon for the Chevy diesel. I have a 6. 2 '83 Suburban and have had this happen several times. It is very difficult to jump. It usually requires two separate vehicles, one jumped to each battery. I keep a big Sears battery charger around and carried it quite a bit because it would usually start it when jumping would not.
One of the causes I found is the high amperage requirement of the starter on the Chevy diesel. I 17 years, 250,000 miles, (150,000 on first engine, 100,000 on second engine - a 1985 engine - after it was stolen) I went through around 6 or 7 starters. When the glow plugs come on while cranking the voltage drops and overheats the starter. And as was said earlier, the side mounts can make it worse. I changed to top mounts early on, but the wires heat up as well and cause voltage drop.