Mac here as well. No issues. Download the zip, OSX has a built in zip extractor.
1.)Download the .zip directly to your flash drive
2.)Double click the .zip file on the flash drive, the file will extract
That's it. The update software (on the pinball) reads directory structure, or you can copy/paste the file from the extracted directory to the root of the USB stick if you want.
Otherwise, flip the dip switch, turn the game on, then follow the on screen prompts.
One quirk for me, when I got to the point where it says "insert flash drive" the game didn't detect it. So with the flash drive in I power cycled the game, re-did the upgrade procedure and didn't have an issue.
One potential Mac related issue could be your thumb drive isn't formatted FAT, but IIRC, OSX will format it FAT by default so you should (should being the key word) be okay.