Both teensy devices should be running the same sketch included below. If the test is performed without the second teensy connected to the USB host port, it will complete successfully. If the second teensy is connected to the USB host port, there is a very high probability that it will fail. Even reducing the frequency that the second teensy sends HID packets to 1 packet / 500 ms still has a high probability of causing the driver to fail.
Tried with a different USB hub and it seems to be working fine.