While there is a lot of issues concerning secure, private and anonymous Internet usage, there is little that focuses upon all the various parameters which may have a direct or even indirect bearing upon the issue.
Let us assume that I use Tails,and let us assume I use Tor on that OS. Now I have an issue with what appears to be confusing and possibly conflicting information.
If I thought that using a VPN would help me, then the information at VPN Support seems to indicate it is not advised.
If I thought that using bridges thru pluggable transports was a good idea, then I would think that I would want Tor to request a bridge automatically from a list. However, that looks like it is not possible to automate that process. At the very least, I must select a built-in bridge, even though the text states, "Unfortunately, because these bridges are publically distributed, it is easy for censors to block some of them, so some of them may not work." Oh goody!
There seems to be too many gotcha's. Exactly what is the best and most automate combination?