Great game! Thank you for it.
I have been planning of making a cow girl training sim myself. My coding skills are pretty nonexistent though, so I'll probably never get anything done... by myself.
I didn't read much of this thread, just the first and the last page so maybe this has been discussed, in which case I'm sorry, but if you think you are going to add some graphics eventually, I would be interested in helping out.
Just throwing out some ideas that popped in my head.
First design of what the game could look like, that came into mind was something like this (please note that this was something I just quickly threw together in 30mins or so):
I was thinking that a completely different window for setting the task for the girls was kind of unnecessary. It could just be a drag-and-drop thing in the upper left corner:
Also the window is a bit crowded. So sliding some of the buttons away from the screen might be a good idea:
