Hey 3B (Hello, By the way) we had that same problem with the '49 4400. Complete new brake system (everything new) with DOT5 fluid, even. Bled the brakes multiple times and then bled them several more times -- couldn't get away from the same mushiness as Pinch. Turned out we hadn't adjusted the brake shoes out enough and it was taking multiple pumps to get them to travel far enough to make contact with the drums. So we took more slack out and the brakes were perfect.
If he's bled the brakes correctly and still having that issue, he might try checking that the adjustment is correct on all the shoes.
Just my limited experience, FWIW.
