Will,
Try reversing the X distances in the program that doesn't work - I see that you have homing set but I am not sure whether you have 'homed'.
Also - and I see a similar issue with mine - what are your MACH values showing?
If you are running the normal default G53 co-ords, the MACH values are shown in smaller text - but these are the ones that are used for keeping within the defined window - and you have software limits set.
So....try physically placing the tool to 0,0,0, then step through to MACH co-ords, do a 'zero all', step back to G53, do another 'zero all', then run your little programme.
I run X and Y to the table physical limits but Z is set by hand each time for a tool change and if I set it such that the MACH co-ords do not permit a retract then nothing moves...
And on that same note, I see that your Z safe height is set to zero which is IMO very unwise since this is usually the height of the top of the surface to machine - the default '5' is far safer.
Best of luck!
Simon