> You should not do this. It is at best useless, at worst strictly negative.
Whenever people write this comment I get the same vibe as when people say that all the recipes in The Anarchist Cookbook are rigged to fail - however I’m in a much better position to judge the technology then the chemistry.
Adding in the VPN (which you should already have and use regularly) before the first Tor guard or bridge node has several benefits - it obscures your usage of the Tor network by a causal observer at the origin (the FBI said they could tell Dread Pirate Roberts was using Tor from the ip addresses, just not what he was using it for - though they did note he was active on Tor during periods Dread Pirate Roberts was active although that alone wasn’t enough for a warrant), it obscures your origin ip to the causal observer at the guard or bridge, your activity is mixed with all other vpn users using the same vpn server(s) - some VPNs add a layer of indirection by routing your traffic through two servers, and it increases the total number of nodes your traffic flows through by at least 1 - unless you do a compile time change to increase the length of the route.
The risk of a party having control of both your vpn and all the tor servers in your path is not zero but at that point the universe pretty much wants you to be found. Should have gone to those Wednesday pot-lucks and put a little more into the building fund. ;)
The person in the article did not use a vpn and they traced the traffic to his mom’s house - amendment to the Ten Commandments of Selling Crack, “Don’t sell crack where your moms at”.
Paying for a vpn with a credit card doesn’t make you identifiable, the list of suspects is everyone who uses the vpn, or knows someone who has a password, or works for a company that maintains a pool of corporate accounts. Most VPNs don’t link outgoing connections to back to users, just so they don’t have to deal with people asking those sorts of questions.