I see plenty of guides on how to do it with the help of your PC. But I have a Mac (and no iPhone) so I'd like to know if its even possible to do from my Mac without having to buy Windows and put it on bootcamp or Parallels.
Idk if you can. I tried awhile back when I first rooted but you need rsd lite which is only available for windows right now. So honestly, the best way would be to see if you can get your hands on a PC it would be much faster than waiting for a root option on mac.
If you're running 2.1 already, you can't do it from a mac tothe best of my knowledge. When I wiped, 2.1 automatically downloaded and I lost root but fortunately I had wife's laptop to use. If you can somehow get back to 2.01, you can then root using a mac- basically just follow the instructions for a pc but do everything from the phone, not through ADB. That's how I did it...it wasn't difficult.
Unfortunately the initial root process with the installation of the SP Tools, it requires the Motorola software. After that install, you can use your Mac to copy files to the SD card on your Droid. You could use VMWare Fusion like I did for the Motorola software, or another VM Windows application or even boot camp.