I am a mac man. From day one (downloading TOR) to trying to get the GPG working, I had nothing but issues. I spent days trying to figure shit out. Tor was pretty easy, but I have windows on my mac, so today, I opened up my pc (via bootcamp) IT took me 1/2hr to set up tor and get the keys running fine. My advise would be to bag the mac and run the pc if you are going to use GPG and TOR. Wish I would have done it sooner. Life is sooo much better..