I am not sure if I am going to help, but I'll give this a shot....
1. I looked in my parts books as well because all of the parts in your diagram seemed strange to me. Just to make it confusing there are a few different revisions of the parts manual so that doesn't make things easy--I did find the one you are using. I am going by memory here, but all I have ever seen on my WD-9's (later production ones) is the rubber insulator between the radiator and the cast frame--no other shims or washers. So I am assuming that yours is the same radiator set up as mine with the cast iron tanks and sides. Again from memory, the rubber washer should be approximately 1/4 inch thick.
2. This is a guess about your problem and maybe you have checked it. The tractor frame holes for the radiator are slotted (going by memory again) and I think I may have had a problem where the upper radiator hose and fan shroud clearance were not right if the radiator was too close to the engine. I may have moved the bottom of the radiator away from the engine slightly. If the bottom of the radiator is too close to the engine, then your radiator may be at a slight angle forwards, causing the bottom of the shroud to be elevated and the top hose connection to be misaligned slightly. Some final adjustments are usually required once the grille and support rod are installed You have probably double/triple checked it already, but thought I should mention it.
Just guessing--I will take a look at one in my shop tomorrow and check the fan/shroud clearance as well.
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