I use Windows, so I can't really help you with your Mac question about the configuration GUI.
Once you get past that hurdle and into Java development then please let me know how you get on. The library relies on usb4java, which claims to have the right native libraries to run on Linux, Windows or OS X, but I've only played around with it on Linux and Windows.
I'm occasionally updating the library but the main Pololu-related stuff should be fairly stable.
Good luck and please let me know how you get on or if you have any further questions.