I'm doing the same myself, a complete new loom for my 41 pu. Ununsulated terminals, and heat shrink when I can. It may not be perfectly as original, but it is functional and smart and looks professional. It's worth getting a good pair of crimpers. I am also using the braided polyester sleeving. It takes a bit of planning if the loom is not dead simple, but I am pleased with my efforts.
In my mind, I wouldn't mind betting the original rubber tubing insulating material required an expander tool. I'm thinking a three pronged tool that expanded the tube to slip over the terminal and is then released and withdrawn.
Pure guesswork, but these were mass produced oem harnesses and special tooling would not have been an issue. I don't know what would have been available to the home gamer back in the 30s and 40s.
Mart.