When the cycle dim option is selected the programming of the button occurs on the release and not the press to allow the system to see the hold command before affecting the lights. If the button was held then the release only stops the cycle dim commands and does not execute the programming. There is also a different command sent to turn the lights on as to turn the lights off from a button press.
The dimmers hearing the command from the keypad and the processor will not cause the issue you are experiencing as they are designed to handle this communication. If the processor(s) are disconnected from the local networks do these issues still occur? If these issue still occurs when the processor(s) are disconnected from the local network please create a support file and send that into
hwsupport@lutron.com indicating which button was being used when the issue occurred.