I currently an running TAILS over a DD-WRT router. It is to my understanding that my ISP can see I am using TOR. I know this is completely fine and all but I still feel it is a little sketchy. Especially if I'm using it a lot.
I have access to a very secure VPN which is overseas and has no logs. Would it be safer to route my connection through this VPN? I've been planning on doing it but have read some controversial posts. Thanks :P
Help is a strange word.
You should be okay without VPN, provided you are taking all other security measures. But, it does give another wall between you and LEO, and VPN is a nice big wall with spikes on top and offensive yet skilfully done graffiti on the side. Especially if you can do it free, do it, even if it only helps your piece of mind.
If you are a vendor, then it's a must have, as vendors are a hundred times more desirable to LEO.