I don't see a big learning curve for Linux.
You can put up CHIRP in about five minutes from the LIVE CD. You add the PPA giving the command line - cut and paste - and you have CHIRP.
You do have to find out the correct usb device number if your connecting via usb.
I could help you with that. Mac and Linux are cousins except on Linux we still have much more functionality with command line which gives us some awesome raw power.