I can't seem to get Tails up and running correctly. I have it on a dvd, and can open it up and use it on restart, but when I try to open up Tor, it says Tor is not ready. I've figured out that it is because when using Tails, I cannot connect to the internet. I then tried restarting and opening more options, and turning off MAC spoofing, but this didn't work either. By the way I am on a Mac. Anyway, I don't think I am going to be able to get it to work, so how fucked am I if I decide to order without Tails? I would only be ordering 2 times a month or so.
I would not trust a Mac even with TOR but I'm very paranoid. Have you tried failsafe mode when booting TAILS?
You have other options, you could try getting on a free wifi. Maybe you router is blocking TOR. You can plug in an ethernet cable directly. Do Macs even have ethernet jacks?
If you do decide not to use TAILS, you MUST use PGP to encrypt your address.