Programmatically talking to a Serial Port in OS X or Linux
/dev/cu.xxxxx is the "callout" device, it's what you use when you establish a connection to the serial device and start talking to it. /dev/tty.xxxxx is the "dialin" device, used for monitoring a port for incoming calls for e.g. a fax listener.
have you tried watching the traffic between the GUI and the serial port to see if there is some kind of special command being sent across? Also just curious, Python is sending ASCII and not UTF-8 or something else right? The reason I ask is because I noticed your quote changes for the strings and in some languages that actually is the difference between ASCII and UTF-8.