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Be sure you have a steel fuel line from the tank up to the engine bay. If someone ran rubber that far instead of steel, it can collapse during the warm season or when it gets old.
After reading your list, My next question would be, Do you have a tillotson or Carter carb ? An answer to your question about typically running hot, is yes, I am also in a hilly area, and they can get quite warm over the hills. I have 5 Crosleys and have the fuel pump shields on all of them. The tillotson carb seems to work better for me when the temps get hot. I have also been changing my upper fuel lines over to the braided flexible steel lines. Quite expensive lines to have made at the hose and belt shop, however, No kinking or suctioning closed when hot, and no breakdown of rubber fuel lines. I would also recommend replacing the rubber in your fuel pump. Our fine suppliers carry the complete fuel pump rebuild kits. crosleyautoclub.com
and look for suppliers.
my 1947 Crosley CC with a replacement CI block has a stubborn tendency to vapor lock. It will do it after long climbs or even if I let it idle with the hood down for 15 minutes or so. It never does it cruising on the level. The cooling system has never boiled over but the gauge does move above normal or to about 3/4 range at least when it vapor locks. I know without a doubt the issue is vapor lock. I have done all of the following without changing the problem much.
1) changed the thermostat
2) recored the radiator with a much more efficient modern core(expensive)
3) rebuilt the water pump
4) installed a fuel pump shield and even wrapped that with aluminum foil for extra reflection
5) Verified the engine timing is spot on
6) doubled up on the isolation gasket between the fuel pump and the and the block
7) carburetor is rebuilt and adjusted properly
8) exhaust system is new from one end to the other
9) The radiator cap is original, I think, and is not a pressure cap
It has been suggested that I remove the square plates on the sides of the block to confirm there is not a sediment issue. I have not done that yet because the engine was recently rebuilt by others and hard to believe that was no cleaned. It is next on my list though. Engine runs good and has good power. I am open to any and all suggestions and wondering if this is a common problem? It is driving me nearly nuts.