I'm not a Mac user, but it seems a lot of your questions are non O/S specific 2. VM or USB? If your using Whonix, Vm. Tails USB 3. Whonix or Tails? My opinion Whonix 4. Mac address spoofing? (Code, Reporting, Implications) ? Cant help you there. 5. Stop outgoing reports? (Console is always trying to call Apple... this is not good.) Not sure 6. SSD or HD? I imagine Mac SSD technology is the same as PC SSD, therefore its not easy to completely remove all files even after deleting. Using a USB with Tails will fix this issue. 7. Advanced OPSEC tuning and leading edge development? (Other Darknet forums, links or think tanks) No Idea 8. Run an encrypted, Truecrypt Lynix partition for all of the deviant stuff, and run a nice and normal partition for the regular porn stuff. yes. Truecypt is cool. run a hidden parition. But if your using Tails on a USB, then no need.