Nothing is ever easy with these cars. For some reason, my wife's new windows 8 box would not do the "discover new hardware" bit so that I could load the USB driver for the S&S ECU software. I fussed around for about an hour wishing that this stuff ran on a Mac in native mood and then I tried her old win 7 machine and it all came together.
More likely a problem with the hardware than the Win 8 operating system. There could always be an incompatibility problem with a driver but it should have been able to recognise that a new device had been attached.
You want to run it on a Mac? Now you really are a masochist. I have had more frustrations with Apple products and trying to get them to work with peripherals than I have ever had with any other operating system.