should I be launching it by running "python chirpw" that was the closest I found by looking in the chirp.desktop to figure out what that was launching.
Yep, that's a fine way to do it.
I've attached the output from launch, setting ic9x to "B", and trying to download from radio. then I selected "new" and again tried to download from radio.
Okay, you might be missing something there.
I didn't find any place to tell it what serial port or other such info I might be using, that might be why it's not working, as it's likely got no idea where my radio's plugged in. I'm assuming that's user error on my part.
When you go to Radio->Open ic9x->Band B (for example), it will bring up the settings box, where the model and file are greyed out. The serial port box is likely empty, so you need to put the path to your device in there. Whatever you use for D-RATS should do the trick there as well. Then you can hit okay and it should load the radio.
I've never actually run CHIRP on the Mac, but several other people have, so it sounds like it should be okay.